Methyl iodide → HCID 22106697, compound

HRID 1377564Notes

Reaction equation

HRID 1377564 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).

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-c6227a7af1134392938063bb9dad4965
Source dataset
uspto-grants-1997_09
Patent number
US05665747

Reaction notes

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