Chlorosulfonic acid → 5-Carbamoyl-2-methoxybenzenesulfonyl chloride

HRID 733353Notes

Reaction equation

HRID 733353 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=1>>[C:12]([C:11]1[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[C:16]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:15]=1)(=[O:13])[NH2:14]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 769594-Methoxybenzamide

Product 1

HCID 159220085-Carbamoyl-2-methoxybenzenesulfonyl chlorideYield 92.8%

Procedure

To 1733 g of chlorosulfonic acid was added in small portions 150 g of 4-methoxybenzamide under ice-cooling with stirring during 15 minutes, and the mixture was stirred at room temperature for 14 hours. After being stirred at 50° C. for additional 1.5 hours, the reaction mixture was dropped into 7 kg of ice. The precipitate was collected by filtration, washed with water and hexane to give 230 g of 5-carbamoyl-2-methoxybenzenesulfonyl chloride.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 14 hours
  3. stirringAfter being stirred at 50° C. for additional 1.5 hours
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water and hexane

Sources & evidence

ORD record
ord-639d20903e2641379d20b369f9a0f42e
Source dataset
uspto-grants-2009_09
Patent number
US07589126B2

Reaction notes

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