Acetyl chloride → N-(3-Bromobenzyl)-N-methylacetamide

HRID 561785

反応式

HRID 561785 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][NH:6][CH3:7].CCN(C(C)C)C(C)C.[C:20](Cl)(=[O:22])[CH3:21]>CN(C)C1C=CN=CC=1.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][N:6]([CH3:7])[C:20](=[O:22])[CH3:21]

参加物

6

反応物 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 457588Benzenemethanamine, 3-bromo-N-methyl-

生成物 1

HCID 57956102N-(3-Bromobenzyl)-N-methylacetamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To a DMF (0.1 M) solution of 3-bromo-N-methylbenzylamine (1 eq.), Hunig's base (3 eq) and 4-(dimethylamino)pyridine (5% loading) was added acetyl chloride (1.5 eq). The resulting reaction mixture was stirred at RT for 16 h. After quenching the reaction with sat. aq. NaHCO3, the mixture was extracted with EtOAc. The organic extract was washed with 10% aq. HCl, sat. aq. NaHCO3, and brine. Drying over Na2SO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a yellow oil. Purification by way of flash chromatography (SiO2, 4:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a yellow oil.

後処理

  1. customThe resulting reaction mixture
  2. customAfter quenching
  3. customthe reaction with sat. aq. NaHCO3
  4. extractionthe mixture was extracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with 10% aq. HCl, sat. aq. NaHCO3, and brine
  7. dry with materialDrying over Na2SO4, filtration and concentration of the filtrate in vacuo
  8. customafforded the crude product as a yellow oil
  9. customPurification by way of flash chromatography (SiO2, 4:1 (v/v) Hex:EtOAc→EtOAc)

出典と根拠

ORDレコード
ord-249c480083964669afc97ff8a33b281e
出典データセット
uspto-grants-2011_11
特許番号
US08063105B2

関連ノート

読み込み中…