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

HRID 1844641Notes

Reaction equation

HRID 1844641 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].[C:17](=O)([O-])[O-].[K+].[K+].CI>CC(=O)CC>[CH3:17][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

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 866857054-bromo-3-chloro-N-trimethylsilanylmethylthiobenzamide

Product 1

HCID 668366594-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzimidic acid methyl esterYield 55.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 4-bromo-3-chloro-N-trimethylsilanylmethylthiobenzamide (Example I13) (4.43 g) in butanone (80 ml) was added potassium carbonate (2.73 g) and methyl iodide (1.02 ml). The reaction mixture was stirred at ambient temperature for 20 hours. The reaction mixture was concentrated and the residue purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:5) to give of 4-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester (2.56 g). 1H-NMR (400 MHz, CDCl3): 7.55-7.15 (m, 3H), 3.55 (s, 2H), 1.98 (s, 3H), 0.00 (s, 9H) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:5)

Sources & evidence

ORD record
ord-9a6bbc02d5284deeb5a1a0a9201baa6a
Source dataset
uspto-grants-2015_02
Patent number
US08946447B2

Reaction notes

Loading…