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

HRID 964159

Reaction equation

HRID 964159 reaction equation
[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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-73037955524647d0a7b68395ab96ebca
Source dataset
uspto-grants-1998_06
Patent number
US05767121

Linked notes

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