1,2-Dichloroethane → 4-chloro-N-phenethylbenzenesulfonamide

HRID 22106Notes

Reaction equation

HRID 22106 reaction equation
C(Cl)CCl.[C:5]1([CH2:11][CH2:12][NH2:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:13][CH2:12][CH2:11][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 1001PhenethylamineHCID 73984-Chlorobenzenesulfonyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 7228614-chloro-N-phenethylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

To a mixture of 150 ml of ethylene chloride and 150 ml of water are added 30.3 g of 2-phenylethylamine, 12 g of sodium hydroxide and 0.5 g of tetrabutylammonium bromide. 65.5 g of 4-chlorobenzenesulphonic acid chloride are added to the mixture in batches with stirring. After 30 minutes the organic phase is separated off, evaporated down and the residue is recrystallised from toluene.

Workup

  1. customAfter 30 minutes the organic phase is separated off
  2. customevaporated down
  3. customthe residue is recrystallised from toluene

Sources & evidence

ORD record
ord-e2abf3686c71440cad7726de2d91b938
Source dataset
uspto-grants-1995_06
Patent number
US05426119

Reaction notes

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