A common compound: 7189-69-7, name is 1,1′-Sulfonyldiimidazole, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 7189-69-7
Methyl 5-(phenethylthio)-2-(l-phenylpiperazine-4-sulfonamido)benzoate (3q) Synthesized using reported procedure with modification (see, e.g., Beaudoin, S.; Kinsey, K. E.; Burns, J. F. J. Org. Chem. 2003, 68, 115-119). To a round-bottom-flask under nitrogen 1- (lH-imidazol-l-ylsulfonyl)-lH-imidazole 14 (80 mg, 0.4 mmol, 2 equiv.) and dry CH2CI2 (10 mL) were added at 0 C. MeOTf (72 mg, 0.05 mL, 0.44 mmol, 2.2 equiv.) was added and then the mixture was stirred for 3 hours. The solvent was removed under reduced pressure and re dissolved in dry CH3CN (10 mL) at room temperature. 1 -Phenylpiperazine (65 mg, 0.061 mL, 0.4 mmol, 2 equiv.) was added and then the mixture was stirred for 16 hours. The reaction mixture was concentrated under reduced pressure. The crude product was dissolved in dry CH2C12 (10 mL) at 0 C. MeOTf (72 mg, 0.05 mL, 0.44 mmol, 2.2 equiv.) was added, followed by stirring the mixture for 2 hours. The solvent was removed under reduced pressure and re dissolved in dry CH3CN (10 mL) at room temperature. Methyl 2-amino-5- (phenethylthio)benzoate 2 (57.5 mg, 0.2 mmol, 1.0 equiv.) was added and then the mixture was heated to reflux for 16 hours. The reaction mixture was then allowed to cool down and concentrated under reduced pressure. The crude product was purified by flash column chromatography (ethyl acetate_hexanes=30:70) on silica gel to afford 3q (75 mg, 73% over 2 steps) as yellow oil which solidified upon standing. lH NMR (300 MHz, CDC13) delta 10.45 (s, 1H), 8.02 (d, J= 2.1 Hz, 1H), 7.68 (d, J= 9.0 Hz, 1H), 7.51 (dd, J = 9.0, 3.0 Hz, 1H), 7.31-7.16 (m, 7H), 6.92-6.86 (m, 3H), 3.94 (s, 3H), 3.44- 3.41 (m, 4H), 3.19-3.11 (m, 6H), 2.92-2.87 (m, 2H); 1 C NMR (75 MHz, CDC13) delta 167.98, 150.59, 139.81, 139.76, 136.43, 132.74, 129.78, 129.22, 128.52, 128.48, 126.53, 120.80, 119.24, 116.79, 115.36, 52.67, 49.07, 46.28, 36.07, 35.64.
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, 7189-69-7, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; NIKOLOVSKA-COLESKA, Zaneta; STUCKEY, Jeanne A.; MADY, Ahmed; MIAO, Lei; (140 pag.)WO2016/172218; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem