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

HRID 241519

反応式

HRID 241519 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[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c293342cb2f44c8c9470e59173be86d6
出典データセット
uspto-grants-2014_02
特許番号
US08653000B2

関連ノート

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