Acetanilide → N-Acetylsulfanilyl chloride

HRID 846302Notes

Reaction equation

HRID 846302 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].S(=O)(=O)(O)N.S(Cl)(Cl)=O>>[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]

Participants

5

Reactant 4

HCID 904AcetanilideHCID 5987Sulfamic AcidHCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acid

Product 1

HCID 8481N-Acetylsulfanilyl chloride

Conditions

Temperature
60 °C

Procedure

135.2 g (1.0 mol) of acetanilide are added in portions to 349.5 g (3.0 mol) of chlorosulfonic acid and 2 g of sulfamic acid such that the temperature remains at 40° C. The mixture is then heated to 60° C. and stirred at this temperature for 60 minutes, then 142.8 g (1.2 mol) of thionyl chloride are added dropwise over the course of 2 hours and the mixture is stirred until evolution of gas has ended. For working up, the mixture is dripped into ice water, and the precipitated crystals are filtered off with suction and washed with water. 394.9 g of 4-acetamidobenzenesulfonyl chloride (water content: 41.7%; chloride content: 58.1%), corresponding to 230.2 g (98.5%) calculated as dry material, having a melting point of 139° C. are obtained.

Workup

  1. customremains at 40° C
  2. stirringthe mixture is stirred until evolution of gas
  3. filtrationthe precipitated crystals are filtered off with suction
  4. washwashed with water
  5. customare obtained

Sources & evidence

ORD record
ord-5666bf093f6e48d9a653aded58f487ed
Source dataset
uspto-grants-1992_08
Patent number
US05136043

Reaction notes

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