Chloroacetanilide → 4-(2-Chloroacetamido)benzene-1-sulfonyl chloride

HRID 1107659Notes

Reaction equation

HRID 1107659 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[Cl:12][S:13](O)(=[O:15])=[O:14].S(Cl)(Cl)=O>>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:13]([Cl:12])(=[O:15])=[O:14])=[CH:8][CH:7]=1)=[O:4]

Participants

4

Reactant 3

HCID 11485ChloroacetanilideHCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acid

Product 1

HCID 187853244-(2-Chloroacetamido)benzene-1-sulfonyl chloride

Conditions

Temperature
65 °C

Procedure

Chloroacetanilide (4.53 g) is slowly added to chlorosulfonic acid (7.5 mL) at a temperature of 5° C. The solution is heated to 65° C. and thionyl chloride (0.78 mL) is added. After 10 minutes of gas evolution the reaction was cooled to room temperature. The mixture is added to ice/water (2.14 g/3.2 mL) and stirred for 30 minutes. The product was filtered, washed with water (60 mL), placed under vacuum at 50° C. and dried to a constant weight. The product is a white powder, yield: 4.81 g (67%).

Workup

  1. temperatureAfter 10 minutes of gas evolution the reaction was cooled to room temperature
  2. filtrationThe product was filtered
  3. washwashed with water (60 mL)
  4. customplaced under vacuum at 50° C.
  5. customdried to a constant weight

Sources & evidence

ORD record
ord-a1b0e1f72c7c4e058f56f080a2e6357c
Source dataset
uspto-grants-2000_05
Patent number
US06063541

Reaction notes

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