Methyl iodide → HCID 22106697, compound

Reaction equation

[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([C:12]1[S:13][CH:14]=[CH:15][N:16]=1)([OH:11])[C:7]([F:10])([F:9])[F:8].[H-].[Na+].[CH3:19]I>C(COC)OC>[CH3:19][O:11][C:6]([C:12]1[S:13][CH:14]=[CH:15][N:16]=1)([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)[C:7]([F:9])([F:10])[F:8]

Participants

Procedure

1, 1-Di(2-thiazolyl) -2,2,2-trifluoroethanol (1 g) was added to a stirred suspension of sodium hydride (80%, 225 mg) in dry dimethoxyethane (50 ml) at 0° C. After 15 minutes, methyl iodide (2.1 g) was added dropwise. The mixture was allowed to warm to room temperature and was then left stirring overnight. The mixture was concentrated by evaporation, then poured into saturated aqueous sodium chloride solution and extracted with dichloromethane. The material thus obtained was purified by flash chromatography to give the title compound as a white solid (950 mg). M.p. 40°-41° C. 13C Nmr (CDCl3) 54.9, 82.9 (g, J 30 Hz), 122.2, 122.8 (q, J 287 Hz), 143.2 and 163.6 ppm. Found: C, 38.7; H, 2.4; N, 9.9. C9H7F3N2OS2 requires C, 38.6; H, 2.5; N, 10.0%