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

HRID 864025
Notes
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Reaction equation

HRID 864025 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 1140TolueneSolvent
HCID 14798
Sodium Hydroxide
Solvent

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-a316a22cb8d949b5842ab7e316b0ef88
Source dataset
uspto-grants-1996_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05561147

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes