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

HRID 1844641

반응식

HRID 1844641 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-9a6bbc02d5284deeb5a1a0a9201baa6a
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946447B2

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