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

HRID 241519

Reaction equation

HRID 241519 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[Cl:16].CI.[C:19]([O-])([O-])=O.[Cs+].[Cs+].O>C1COCC1>[CH3:19][S:7][C:6](=[N:8][CH2:9][Si:10]([CH3:12])([CH3:13])[CH3:11])[C:5]1[CH:14]=[CH:15][C:2]([Br:1])=[C:3]([Cl:16])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 866857054-bromo-3-chloro-N-trimethylsilanylmethylthiobenzamide

Product 1

HCID 668366594-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzimidic acid methyl esterYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzamide (10.40 g, 30.88 mmol) in THF (200 mL) was added methyl iodide (5.77 mL, 13.15 g, 92.7 mmol) and Cs2CO3 (30.19 g, 92.7 mmol) at −5° C. After 1 h at this temperature, the mixture was heated at 40° C. 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 (8.25 g), which was used in the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-c293342cb2f44c8c9470e59173be86d6
Source dataset
uspto-grants-2014_02
Patent number
US08653000B2

Linked notes

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