1-Bromo-4-chlorobutane → 1,2-bis[N-(4-chlorobutyl)-N-propionylamino]benzene

HRID 274727

反応式

HRID 274727 の反応式
[C:1]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13](=[O:16])[CH2:14][CH3:15])(=[O:4])[CH2:2][CH3:3].Br[CH2:18][CH2:19][CH2:20][CH2:21][Cl:22]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.[OH-].[Na+]>[Cl:22][CH2:21][CH2:20][CH2:19][CH2:18][N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]([C:13](=[O:16])[CH2:14][CH3:15])[CH2:18][CH2:19][CH2:20][CH2:21][Cl:22])[C:1](=[O:4])[CH2:2][CH3:3]

参加物

6

反応物 2

HCID 813641-Bromo-4-chlorobutaneHCID 694922N-[2-(propanoylamino)phenyl]propanamide

生成物 1

HCID 190792541,2-bis[N-(4-chlorobutyl)-N-propionylamino]benzene収率 12.6%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

To a suspension of 3.27 g (15 mmol) of 1,2-dipropionylaminobenzene, 4.32 ml (37.5 mmol) of 4-bromo-1-chlorobutane, and 0.96 g (3.0 mmol) of tetrabutylammonium bromide in 25 ml of toluene, 5.6 ml of 50% aqueous sodium hydroxide was added at room temperature, and the mixture was stirred for 16 hours. The organic layer was separated, washed with saturated aqueous sodium chloride, and dried. The solvent was distilled off and the residue was purified by column chromatography (eluent: hexane/ethyl acetate=2:1 to 1:1 to 1:2 to 1:4) to give 0.76 g of the desired product (12.6% yield, white crystals).

後処理

  1. additionwas added at room temperature
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. customdried
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: hexane/ethyl acetate=2:1 to 1:1 to 1:2 to 1:4)

出典と根拠

ORDレコード
ord-d5d9ac95fbb94fb3ace7bcc65e63f621
出典データセット
uspto-grants-1995_02
特許番号
US05389658

関連ノート

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