Category: 20075-26-7

Application of 20075-26-7,Some common heterocyclic compound, 20075-26-7, name is 1-(Methoxymethyl)-1H-imidazole, molecular formula is C5H8N2O, 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.

A. Preparation of alpha-(2,4-dichlorophenyl)-1-(methoxymethyl)-alpha-phenylimidazole-2-methanol This compound was prepared by the procedure described in Example XXVII B, using the following materials: 9.8 g (0.088 mol) of 1-(methoxymethyl)imidazole, 10.4 g (0.09 mol) of N,N,N’,N’-tetramethylethylenediamine, 100 ml. of anhydrous tetrahydrofuran, 62 ml. (0.10 mol) of 15% butyl lithium in n-hexane, 22.6 g (0.09 mol) of 2,4-dichlorobenzophenone in 100 ml. of anhydrous tetrahydrofuran. The reaction mixture was decomposed with 75 ml. of water. The solid matter formed was filtered off and the aqueous phase of the filtrate was discarded. The organic phase was concentrated. The residue appeared to be identical to the solid matter filtered off. The combined solid substances were crystallized from isopropyl alcohol. alpha-(2,4-Dichlorophenyl)-1-(methoxymethyl)-alpha-phenylimidazole-2-methanol was obtained. Melting point 161-161.5 C.

The synthetic route of 20075-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gist-Brocades N.V.; US4152441; (1979); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 20075-26-7, A common heterocyclic compound, 20075-26-7, name is 1-(Methoxymethyl)-1H-imidazole, molecular formula is C5H8N2O, 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.

A. Preparation of 1-(methoxymethyl)-alpha-phenyl-alpha-(p-trifluoromethyl-phenyl)imidazole-2-methanol. A butyllithium solution, prepared from 1.02 g. (0.145 g. at.) of lithium and 7.9 g. (0.058 mol) of butyl bromide in 70 ml. of anhydrous diethyl ether, was added drop-wise at -60 C. to -65 C. under a nitrogen atmosphere to a solution of 4.9 g. (0.044 mol) of 1-(methoxymethyl)imidazole and 3.1 g. (0.044 mol) of N,N,N’,N’-tetramethylethylenediamine in 125 ml. of anhydrous tetrahydrofuran. The reaction mixture was kept standing for 2 hours at -60 to -65 C. and then 11 g. (0.044 mol) of 4-(trifluoromethyl)benzophenone, dissolved in 75 ml. of anhydrous tetrahydrofuran, were added drop-wise. The temperature was maintained at -65 C. for one hour and then the reaction mixture was allowed to attain room temperature overnight. 10 ml. of water and solid carbon dioxide were added and the solvent was distilled off. The residue was dissolved in dilute hydrochloric acid, the solution was washed with diethyl ether and made alkaline with potassium carbonate. The solid substance formed was filtered off and dissolved in chloroform. The solution was washed with water, dried over sodium sulphate and concentrated by evaporation of the solvent. The residue was crystallized from isopropyl alcohol. 1-(Methoxymethyl)-alpha-phenyl-alpha-(p-trifluoromethyl-phenyl)imidazole-2-methanol was obtained. Melting point 158-159 C.

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:
Patent; Gist-Brocades N.V.; US4152441; (1979); 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. 20075-26-7, name is 1-(Methoxymethyl)-1H-imidazole, A new synthetic method of this compound is introduced below., name: 1-(Methoxymethyl)-1H-imidazole

Step B. N-Methyl-N-{4-[2,2,2-trifluoro-1-hydroxy-1-(1-methoxymethyl-1H-imidazol-2-yl)-ethyl]-phenyl}-benzenesulfonamide To a solution of 55 mg (0.49 mmol) of 1-methoxymethyl-1H-imidazole in 5 ml of THF at -78 C. was added 0.20 ml (0.50 mmol) of a 2.5 M solution of n-butyllithium in hexanes and the resultant mixture was stirred at -78 C. for 30 mins.After this time, a solution of 160 mg (0.47 mmol) of N-methyl-N-(4-trifluoroacetyl-phenyl)-benzenesulfonamide (Example 22, Step A) in 2 ml of THF was added and the resultant mixture stirred at -78 C. for a further 2 h, and then at room temperature for 14 h.After this time the reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and the filtrate was concentrated.The residue was purified by chromatography on silica gel (hexanes:EtOAc, 4:1) to give the title compound. 1H-NMR (CDCl3) delta 3.09 (s, 3H), 3.19 (s, 3H), 4.90 (s, 2H), 5.16 (brs, 1H), 7.07-7.16 (m, 4H), 7.42-7.62 (m, 7H).Mass Spectrum (CI+) m/e=456.1 (M+1).

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.

Electric Literature of 20075-26-7, A common heterocyclic compound, 20075-26-7, name is 1-(Methoxymethyl)-1H-imidazole, molecular formula is C5H8N2O, 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.

The title compound was prepared as follows. To a solution of 1-methoxymethyl- imidazole (216 mg, 1. 95 MMOL) in dry THF (20 mi) AT-78 C was added slowly a solution of t- butyllithium (2. 4 ml of 1. 7 M in THF). After 20 minutes, ZNCI2 (663 mg, 4. 86 MMOL) was added, the mixture was allowed to warm to room temperature and stirred for another 60 min. 1- 4-AMINO-2- [1- (6-CHLORO-PYRIDINE-3-SULFONYL)-PIPERIDIN-4-YLAMINO]-THIAZOL-5-YL}-1-PHENYL- methanone (Example F21 ; 200 mg, 0. 390 MMOL) AND TETRAKIS (TRIPHENYLPHOSPHINO) PALLADIUM (0) (Pd (Ph3P) 4 ; 12 mg, 0. 013 MMOL) were added and the mixture REFLUXED under argon for 2 hours. The solvent was removed and a solution of the resultant residue in ethyl acetate was washed with 0. 1 NAOH, dried over MGS04, filtered, and concentrated. The resultant solid was dissolved in a solution of 38% HCI (10 ML), ethanol (15 MI), and H20 (15 ml) and REFLUXED for 2 hours. The solvent was removed and a solution of the resultant residue in ethyl acetate was washed with sat. NaHCO3, dried over MGS04, filtered, concentrated, and purified via preparative HPLC. The concentrate from fractions was dissolved in EtOAc, washed with sat NAHC03, dried over MGS04, filtered, and concentrated. The resultant solid was placed in acetonitrile (30 ML), water (90 ML), and 38% HCI (0. 5 mL) and evaporated to give 26 mg of white powder in 11 % yield. ‘H NMR (CD30D) : 8 9. 13 (d1H, J=2. 5 Hz), 8. 44 (dd, 1H, J=2. 5, 8. 3 Hz), 8. 23 (d, 1H, J=8. 3 Hz), 7. 78 (s, 2H), 7. 50-7. 40 (m, 1H), 7. 08-6. 97 (m, 2H), 4. 02-3. 90 (m, 3H), 2. 98-2. 87 (m, 2H), 2. 37-2. 13 (m, 2H), 1. 96-1. 78 (m, 2H). ESIMS (MH+) : 546. Anal. Calcd for C23H2, F2N703S2 O 2. 4 HCI * 1. 0 H2O # 0. 5 EtOAc : C, 43. 19 ; H, 4. 26 ; N, 14. 10 ; S, 9. 23. Found : C, 42. 85 ; H, 4. 67 ; N, 14. 50 ; S, 9. 27.

The synthetic route of 20075-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2004/74283; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem