p-Toluenesulfonic acid → HCID 13869332, compound

HRID 1388196Notes

Reaction equation

HRID 1388196 reaction equation
[CH3:1][C:2]1[S:6][C:5]([S:7](=[O:10])(=[O:9])[NH2:8])=[C:4]([C:11]([OH:13])=O)[CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[S:6][C:5]2[S:7](=[O:10])(=[O:9])[NH:8][C:11](=[O:13])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 20471877HCID 20471877, compound

Product 1

HCID 13869332HCID 13869332, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.1 gm (0.45 millimols) of 5-methyl-2-sulfamoyl-thiophene-3-carboxylic acid, 50 ml of anhydrous toluene and 5 mgm of p-toluene-sulfonic acid was heated for 10 hours in a vessel equipped with a water trap. The reaction mixture was evaporated to dryness in vacuo and separated by column chromatography. 0.40 mgm (49% of theory) of 5-methyl-thieno[3,2-d]isothiazole-3(2H)-one-1, 1-dioxide were obtained.

Workup

  1. temperaturewas heated for 10 hours in a vessel
  2. customequipped with a water trap
  3. customThe reaction mixture was evaporated to dryness in vacuo
  4. customseparated by column chromatography

Sources & evidence

ORD record
ord-7c77e99adfce41a3b143454b120a75b1
Source dataset
uspto-grants-1984_02
Patent number
US04430355

Reaction notes

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