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

HRID 1490364Notes

Reaction equation

HRID 1490364 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-67782c2be1ce455088bebafa349fdd7c
Source dataset
uspto-grants-1997_10
Patent number
US05681961

Reaction notes

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