N,N-Dimethylaniline → N-[4-benzyloxy-2,6-bis(trifluoromethyl)phenyl]-2-bromoacetamide

HRID 1373735ノート

反応式

HRID 1373735 の反応式
CN(C)C1C=CC=CC=1.[Br:10][CH2:11][C:12](Br)=[O:13].[CH2:15]([O:22][C:23]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[C:26]([NH2:27])=[C:25]([C:34]([F:37])([F:36])[F:35])[CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH2:15]([O:22][C:23]1[CH:24]=[C:25]([C:34]([F:36])([F:37])[F:35])[C:26]([NH:27][C:12](=[O:13])[CH2:11][Br:10])=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:29]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

5

反応物 3

HCID 949N,N-DimethylanilineHCID 61147Bromoacetyl bromideHCID 210756004-Benzyloxy-2,6-bis(trifluoromethyl)aniline

生成物 1

HCID 21075603N-[4-benzyloxy-2,6-bis(trifluoromethyl)phenyl]-2-bromoacetamide収率 64.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Under an argon atmosphere, N,N-dimethylaniline (2.78 mL, 21.9 mmol) and bromoacetyl bromide (1.91 mL, 21.9 mmol) were added dropwise to a solution of 4-benzyloxy-2,6-bis(trifluoromethyl)aniline (4.90 g, 14.6 mmol) in anhydrous toluene (150 mL) under ice cooling. Immediately after the dropwise addition, the mixture was heated under reflux and then stirred for 1 hour. After cooling, the reaction mixture was filtered through Celite and the insoluble matter was washed with toluene. The residue obtained by distilling the filtrate under reduced pressure was purified by chromatography on a silica gel column (developing solvent; hexane:acetone=10:1→6:1→5:1). The crude product thus obtained was recrystallized from hexane-acetone, whereby 4.31 g (yield: 64.7%) of N-[4-benzyloxy-2,6-bis(trifluoromethyl)phenyl]-2-bromoacetamide was obtained as colorless needle-like crystals.

後処理

  1. additionImmediately after the dropwise addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was filtered through Celite
  6. washthe insoluble matter was washed with toluene
  7. customThe residue obtained
  8. distillationby distilling the filtrate under reduced pressure
  9. customwas purified by chromatography on a silica gel column (developing solvent; hexane:acetone=10:1→6:1→5:1)
  10. customThe crude product thus obtained
  11. customwas recrystallized from hexane-acetone

出典と根拠

ORDレコード
ord-758d94ad5a20437e9bbeb57198c2ac0d
出典データセット
uspto-grants-2007_01
特許番号
US07163944B2

反応ノート

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