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

HRID 241512ノート

反応式

HRID 241512 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6d8e38ed5a04490a966099cbd3d285a3
出典データセット
uspto-grants-2014_02
特許番号
US08653000B2

反応ノート

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