Benzene → N-Methyl-N-(tert-butyldimethylsilyl)trifluoroacetamide

HRID 358378ノート

反応式

HRID 358378 の反応式
C1C=CC=CC=1.[CH3:7][NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11].[H-].[Na+].[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>C(#N)C>[CH3:7][N:8]([Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[C:9](=[O:14])[C:10]([F:13])([F:12])[F:11]

参加物

6

反応物 4

HCID 241BenzeneHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 69948Acetamide, 2,2,2-trifluoro-N-methyl-

生成物 1

HCID 2724275N-Methyl-N-(tert-butyldimethylsilyl)trifluoroacetamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To 800 ml of dry benzene:acetonitrile (v/v, 1:1) was added 127 g (1.0 mole) of N-methyl-trifluoroacetamide. To this solution, while stirring and maintaining the temperature at 0 degress C., was slowly added 23.5 g (0.98 mole) of sodium hydride. The solution was then stirred for 4 hours at 4 degrees C. At this time, 173.34 g (1.15 mole) of t-butyldimethylsilyl chloride was added in four equal aliquots over a period of 80 minutes. After the last addition the solution was stirred for 2 hours at 4 degrees C. The precipitate of sodium chloride was then removed from the reaction mixture by filtration under dry nitrogen and the resulting filter cake washed twice with 100 ml each of dry benzene. Washings and filtrate were combined and concentrated. The remaining yellow solution was fractionally distilled with the distillate at 158-172 degrees C. being collected. Redistillation of this fraction gave the desired product.

後処理

  1. temperaturemaintaining the temperature at 0 degress C
  2. stirringThe solution was then stirred for 4 hours at 4 degrees C
  3. additionAfter the last addition the solution
  4. stirringwas stirred for 2 hours at 4 degrees C
  5. customThe precipitate of sodium chloride was then removed from the reaction mixture by filtration under dry nitrogen
  6. filtrationthe resulting filter cake
  7. washwashed twice with 100 ml each of dry benzene
  8. concentrationconcentrated
  9. distillationThe remaining yellow solution was fractionally distilled with the distillate at 158-172 degrees C
  10. custombeing collected
  11. distillationRedistillation of this fraction

出典と根拠

ORDレコード
ord-42fe8ff05edf4687a2f49e3dbd7652d5
出典データセット
uspto-grants-1984_08
特許番号
US04467037

反応ノート

読み込み中…