Category: 7189-69-7

These common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Application In Synthesis of 1,1′-Sulfonyldiimidazole

General procedure: A solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

The synthetic route of 1,1′-Sulfonyldiimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7189-69-7, These common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

The synthetic route of 7189-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7189-69-7, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 7189-69-7, name is 1,1′-Sulfonyldiimidazole, This compound has unique chemical properties. The synthetic route is as follows.

A 20-mL vial was charged with N-(4-methoxybenzyl)-2-methylpyrimidin-4-amine (prepared analogous to Intermediate A, pages 43-44 of WO2013122897, wherein l,2,4-thiadiazol-5-amine was replaced with 2-methylpyrimidin-4-amine and 2,4-dimethoxybenzaldehyde was replaced with 4-methoxybenzaldehyde) (864 mg, 4.36 mmol) then purged with nitrogen. 2-Methyltetrahydrofuran (10.0 mL) and a solution of lithium hexamethyldisilazide in THF (1.0 M, 4.27 mL, 4.27 mmol) were added via syringe to the stirred reaction mixture. The vial was sealed with a Teflon coated cap and the reaction was warmed to 90 C and stirred vigorously. After 2 h, the red reaction mixture was allowed to cool to ambient temperature. The reaction mixture was diluted with water (25 mL) and EtOAc (25 mL). The layers were separated and the aqueous layer extracted with additional EtOAc (2 x 25 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and purified by flash column chromatography (100-g silica gel Biotage column, eluent: gradient, 20 to 80% 3:1 EtOAc/EtOH in heptane with DCM as a 10% additive) to afford N-(4-methoxybenzyl)-N-(2-methylpyrimidin-4-y 1)-1 H-imidazole-1 -sulfonamide (450 mg, 1.25 mmol, 57.4 % yield) asa light-yellow solid, m/z (ESI) 360.2 (M+H)+

The chemical industry reduces the impact on the environment during synthesis 1,1′-Sulfonyldiimidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 7189-69-7, The chemical industry reduces the impact on the environment during synthesis 7189-69-7, name is 1,1′-Sulfonyldiimidazole, I believe this compound will play a more active role in future production and life.

Compound B4 (137 mg, 0.240 mmol) obtained in Step 1 of Example 42 was suspended in toluene (2.4 mL), 1,1?-sulfonyldiimidazole (190 mg, 0.960 mmol) was added, and the mixture was refluxed for 6 days. A 1 mol/L aqueous sodium hydroxide solution was added to the reaction mixture. Extraction with dichloromethane and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate: 100%) to give Compound B8 (19.3 mg, 13% yield).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1,1′-Sulfonyldiimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; Fukuda, Yuichi; Kanai, Toshimi; Nakasato, Yoshisuke; Kimpara, Keisuke; US2013/65905; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7189-69-7, These common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step A 1-[(1-Aziridinyl)methyl]-2(S)-butyl-4-(1-naphthoyl) piperazine A solution of 1-(2(R)-butoxycarbonylamino-3-hydroxypropyl)-2(S)-butyl-4-(1-naphthoyl)piperazine (1.67 g, 3.56 mmol) in dimethylformamide (10 mL) was cooled to 0 C. under nitrogen. Sodium hydride (0.427 g, 10.6 mmol, 60% dispersion in oil) was added, followed by 1,1′-sulfonyldiimidazole (0.704 g, 3.56 mol). The reaction was warmed to 20 C. for 1 h, cooled to 0 C. and quenched with water. Dimethylformamide was distilled in vacuo, and the residue partitioned between ethyl acetate and water. The organic phase was washed with saturated brine and dried over magnesium sulfate. The crude product was chromatographed on silica gel with 70% ethyl acetate in hexane, followed by 5% methanol in chloroform. The title compound was obtained as the major product, FAB ms (m+1) 352. A lesser amount of 1-[(1-butoxycarbonylaziridinyl)methyl]-2(S)-butyl-4-(1-naphthoyl)piperazine was also isolated.

Statistics shows that 1,1′-Sulfonyldiimidazole is playing an increasingly important role. we look forward to future research findings about 7189-69-7.

Reference:
Patent; Merck & Co., Inc.; US5856326; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7189-69-7, These common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step A 1-[(1-Aziridinyl)methyl]-2(S)-butyl-4-(1-naphthoyl) piperazine A solution of 1-(2(R)-butoxycarbonylamino-3-hydroxypropyl)-2(S)-butyl-4-(1-naphthoyl)piperazine (1.67 g, 3.56 mmol) in dimethylformamide (10 mL) was cooled to 0 C. under nitrogen. Sodium hydride (0.427 g, 10.6 mmol, 60% dispersion in oil) was added, followed by 1,1′-sulfonyldiimidazole (0.704 g, 3.56 mol). The reaction was warmed to 20 C. for 1 h, cooled to 0 C. and quenched with water. Dimethylformamide was distilled in vacuo, and the residue partitioned between ethyl acetate and water. The organic phase was washed with saturated brine and dried over magnesium sulfate. The crude product was chromatographed on silica gel with 70% ethyl acetate in hexane, followed by 5% methanol in chloroform. The title compound was obtained as the major product, FAB ms (m+1) 352. A lesser amount of 1-[(1-butoxycarbonylaziridinyl)methyl]-2(S)-butyl-4-(1-naphthoyl)piperazine was also isolated.

Statistics shows that 1,1′-Sulfonyldiimidazole is playing an increasingly important role. we look forward to future research findings about 7189-69-7.

Reference:
Patent; Merck & Co., Inc.; US5856326; (1999); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 7189-69-7, name is 1,1′-Sulfonyldiimidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 1,1′-Sulfonyldiimidazole

General procedure: A solution of 500 mg (4.46 mmol) of 2-fluorophenol 1.769 g (8.92 mmol) of 1,1?-sulfonyldiimidazole in 15 mL of tetrahydrofuran was treated with 727 mg (2.23 mmol) of cesium carbonate. The reaction was stirred for 12 h, concentrated, and the residue was partitioned between the ethyl acetate and water (10 mL each). The organic layer was washed sequentially with saturated ammonium chloride solution and brine. After drying over the anhydrous sodium sulfate, the organic layer was concentrated and chromatographed on silica with 1:5 ethyl acetate / hexane as the eluant to afford 880 mg (90%) of 11bas a clear oil:

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Yang, Baocheng; Sun, Zhexun; Liu, Changzhi; Cui, Yan; Guo, Zhilei; Ren, Yuwei; Lu, Zhijian; Knapp, Spencer; Tetrahedron Letters; vol. 55; 49; (2014); p. 6658 – 6661;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 7189-69-7, name is 1,1′-Sulfonyldiimidazole, belongs to imidazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 7189-69-7, name: 1,1′-Sulfonyldiimidazole

NaH (60% in oil, 0.070g, 1.76mmol) was added to a stirred solution of compound 13 (0.23g, 0.16mmol) in dry DMF (3.5mL) at room temperature. After 1h, the suspension was cooled at -40C and 1,1?-sulfonyl-diimidazole (0.22g, 1.12mmol) in dry DMF (1.5mL) was added. After 24h the reaction mixture was quenched with MeOH and allowed to warm to room temperature, then diluted with water (40mL). The mixture was extracted with AcOEt (3×50mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. Flash chromatography (hexane/AcOEt, 7:3) of the crude product gave trisaccharide 14 (0.21g, 85%) as an amorphous solid. [alpha]D20=+1.8 (c=1 in chloroform). 1H NMR (CDCl3): delta=7.94 (br s, 1H, Im), 7.53-7.10 (m, 45H, arom), 7.00 (m, 2H, Im), 5.46 (s, 1H, PhCH), 5.25-5.12 (m, 3H, H-1? and CH2Ph), 4.97 (d, 1H, J=11.1Hz, CH2Ph), 4.85-4.58 (m, 10H, H-1 and CH2Ph), 4.58-4.44 (m, 4H, H-2? and CH2Ph), 4.32 (d, 1H, J1?,2?=7.9Hz, H-1?), 4.23 (dd, 1H, J5?,6?=4.9Hz, J6a?,6b?=10.6Hz, H-6a?), 4.16-4.09 (m, 1H, CH2Ph), 4.09-3.80 (m, 5H, H-2, 3, 3?, 4?, 5?), 3.75-3.52 (m, 5H, H-a, 4, 5, 2?,4?), 3.52-3.20 (m, 7H, H-a?, c, c?, 6a?, 6b?, 3?, 6b?), 3.10-2.98 (m, 1H, H-5?), 1.91-1.69 (m, 2H, 2H-b), 1.29-1.21 (br d, 3H, 3H-6). 13C NMR (CDCl3): delta=155.6 (C=O), 139.1-136.5 (9C, arom), 136.8 (C Im),129.2-126.0 (46C, arom.), 118.6 (C Im), 101.4 (CHPh), 98.6 (C-1?), 98.2 (C-1), 97.1 (br s, C-1?), 85.7 (C-2?), 81.9 (C-4?), 80.3 (br s, C-4), 79.5 (C-3?), 79.2 (C-2?), 78.4 (br s, C-3), 76.7 (C-3?), 76.5 (br s, C-2), 76.2 (C-4?), 75.2 (2C, CH2Ph), 74.6 (br s, CH2Ph), 74.3 (CH2Ph), 73.6 (CH2Ph), 73.1 (br s, CH2Ph), 70.2 (C-5?), 68.4 (C-6?), 68.3 (C-5), 67.3 (C-6?), 67.2 (CH2Ph), 65.7 (C-5?), 65.2 (C-a), 50.8 and 50.5 (NCH2Ph), 44.6 and 43.7 (C-c), 28.4 and 27.9 (C-b), 18.0 (C-6). MS (ESI) m/z (%): 1550.3 (100) [M+NaM+Na]+. HRMS (ESI): m/z calcd for C88H93N3O19NaS 1550.6022 [M+Na]+, found 1550.6055

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1,1′-Sulfonyldiimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Morelli, Laura; Fallarini, Silvia; Lombardi, Grazia; Colombo, Cinzia; Lay, Luigi; Compostella, Federica; Bioorganic and Medicinal Chemistry; vol. 26; 21; (2018); p. 5682 – 5690;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 7189-69-7, These common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

EXAMPLE 5 A solution of 9.79 g (30 mmol) of (7RS,7aR)-3-phenyl-6-benzyl-7,7a-dihydro-7-hydroxy-1H,3H-imidazo[1,5-c]thiazol-5(6H)-one in 100 ml of tetrahydrofuran is added dropwise to a suspension of 0.96 g (32 mmol) of 80% pure sodium hydride in 20 ml of tetrahydrofuran at room temperature under nitrogen and the solution formed is stirred at room temperature for 45 minutes. A solution of 6.34 g (32 mmol) of 1,1-sulfonyldiimidazole in 80 ml of tetrahydrofuran is then added dropwise at room temperature in the course of 10 minutes and the mixture is stirred for a further 20 minutes. The mixture is concentrated, 200 ml of ice-water are added to the residue and the mixture is extracted three times with 100 ml of diethyl ether each time. The combined organic phases are dried over sodium sulfate and concentrated under reduced pressure. Chromatography of the residue on silica gel (ethyl acetate) gives 8.1 g of (7R,7aR)-3-phenyl-6-benzyl-7,7a-dihydro-7-(imidazol-1-ylsulfonyloxy)-1H,3H-imidazo[1,5-c]thiazol-5(6H)-one as an oil. [alpha]36520 =-710, c=1 (methanol).

Statistics shows that 1,1′-Sulfonyldiimidazole is playing an increasingly important role. we look forward to future research findings about 7189-69-7.

Reference:
Patent; Merck Patent Gesellschaft mit Beschrankter Haftung; US4877882; (1989); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 7189-69-7, name is 1,1′-Sulfonyldiimidazole, molecular formula is C6H6N4O2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C6H6N4O2S

(I) 1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranose (3)(1.0 g; 4.0 mmol) was dissolved in DMF (20 ml), cooledat 0 C and under N2-atmosphere NaH (0.14 g; 6.0 mmol)was added to the solution. The suspension was stirred for30 min and cooled to -35 to -40 C. After N?,N-sulfonyldiimidazole(1.2 g; 6.0 mmol) in DMF (12 ml) was droppedto the reaction mixture and stirred for 30 min again at-40 C. MeOH was added (0.8 ml) to the solution andstirred for 30 min at -40 C. The solution was poured intoice-water (200 ml). The precipitate was filtered, washedwith cold water to get the white crystalline product 11(1.2 g; 80%). M.p.: 97-98 C; lit. m.p. (Vatle and Hanessian1996): 98-99 C; Rf = 0.70 (EtOAc-hexane 1:1).(II) From 3 (25.0 g; 96.0 mmol) the yield was 84% (31.5 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7189-69-7, its application will become more common.

Reference:
Article; Nagy, Adrienn; Csordas, Barbara; Zsoldos-Mady, Virag; Pinter, Istvan; Farkas, Viktor; Perczel, Andras; Amino Acids; vol. 49; 2; (2017); p. 223 – 240;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem