Water → HCID 5056961, compound

HRID 1356692Notes

Reaction equation

HRID 1356692 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)[CH3:2].[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.O>N1C=CC=CC=1>[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][S:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)(=[O:11])=[O:10])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 78124-ChloroanilineHCID 5709594-Ethylbenzene-1-sulfonyl chloride

Product 1

HCID 5056961HCID 5056961, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-ethylbenzenesulfonyl chloride (90%, 4.25 g (20.8 mmol)) in pyridine (10 ml), 4-chloroaniline (2.55 g (20.0 mmol)) was added with stirring at room temperature. After 18 hours' stirring at room temperature, water (100.0 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with dilute hydrochloric acid, water and a saturated aqueous solution of sodium chloride successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 5.26 g (89%) of 4′-chloro-4-ethylbenzenesulfonanilide as white crystals.

Workup

  1. stirringAfter 18 hours' stirring at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with dilute hydrochloric acid, water
  4. dry with materiala saturated aqueous solution of sodium chloride successively, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7043b0446ae14c389eb78fbbfb8948b8
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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