Methyl iodide → HCID 22106697, compound

HRID 1456342Notes

Reaction equation

HRID 1456342 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

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9860114HCID 9860114, compound

Product 1

HCID 22106697HCID 22106697, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

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%

Workup

  1. waitwas then left
  2. concentrationThe mixture was concentrated by evaporation
  3. additionpoured into saturated aqueous sodium chloride solution
  4. extractionextracted with dichloromethane
  5. customThe material thus obtained
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-c8790352e6ee4f11b1b76e781d9976fd
Source dataset
uspto-grants-1998_12
Patent number
US05843971

Reaction notes

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