Water → 4-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester

HRID 241512Notes

Reaction equation

HRID 241512 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=[S:7])=[CH:4][C:3]=1[CH3:16].CI.[C:19]([O-])([O-])=O.[Cs+].[Cs+].O>C1COCC1>[CH3:19][S:7][C:6](=[N:8][CH2:9][Si:10]([CH3:11])([CH3:12])[CH3:13])[C:5]1[CH:14]=[CH:15][C:2]([Br:1])=[C:3]([CH3:16])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 866910454-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzamide

Product 1

HCID 668366694-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzimidic acid methyl esterYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzamide (5.00 g, 15.8 mmol) in THF (30 mL) was added methyl iodide (1.97 mL, 4.49 g, 31.6 mmol) and Cs2CO3 (10.3 g, 31.6 mmol) at −5° C. After 1 h at this temperature, the mixture was allowed to reach room temperature and stirred over night. Water was added and the mixture was extracted three times with MTBE. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by filtration over a short plug of silica gel to give the title compound (4.4 g), which was used in the next step without further purification.

Workup

  1. customto reach room temperature
  2. extractionthe mixture was extracted three times with MTBE
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. filtrationThe residue was purified by filtration over a short plug of silica gel

Sources & evidence

ORD record
ord-6d8e38ed5a04490a966099cbd3d285a3
Source dataset
uspto-grants-2014_02
Patent number
US08653000B2

Reaction notes

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