Acetanilide → N-Acetylsulfanilyl chloride

HRID 981453Notes

Reaction equation

HRID 981453 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Cl:11][S:12](O)(=[O:14])=[O:13]>N1C=CC=CC=1>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:12]([Cl:11])(=[O:14])=[O:13])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH2:5]([NH2:4])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:9][CH2:10][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 904AcetanilideHCID 24638Chlorosulfonic acid

Product 2

HCID 8481N-Acetylsulfanilyl chlorideHCID 13583Dodecylamine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Twenty grams of 4-acetylaminophenylsulfonyl-chloride obtained from acetanilide and chlorosulfonic acid and 6.5 g of dodecylamine and 8.1 g of pyridine were added to 100 ml of acetonitrile, and the mixture was refluxed with heating for 3.5 hours. The solvent was distilled off under reduced pressure. 100 ml of ethyl acetate were added to this, and the organic phase was washed with a 5% potassium carbonate solution and a 1% hydrochloric acid solution, and then washed with water. After dehydration of the product by magnesium sulfate, the ethyl acetate was distilled off, whereby 17.7 g of a crude product was obtained.

Sources & evidence

ORD record
ord-a7c913a7a3bc42198f72f9b8c550ee1d
Source dataset
uspto-grants-1991_02
Patent number
US04992360

Reaction notes

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