3-Thiophenecarboxylic acid, 4-(aminosulfonyl)-, methyl ester → thieno[3,4-d]isothiazol-3(2H)-one 1,1-dioxide

HRID 436829Notes

Reaction equation

HRID 436829 reaction equation
[S:1]([C:5]1[C:6]([C:10]([O:12]C)=O)=[CH:7][S:8][CH:9]=1)(=[O:4])(=[O:3])[NH2:2]>C[O-].[Na+]>[O:12]=[C:10]1[C:6]2=[CH:7][S:8][CH:9]=[C:5]2[S:1](=[O:4])(=[O:3])[NH:2]1

Participants

3

Reactant 1

HCID 30422843-Thiophenecarboxylic acid, 4-(aminosulfonyl)-, methyl ester

Product 1

HCID 12593672thieno[3,4-d]isothiazol-3(2H)-one 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

31.6 g (0.143 mole) of methyl 4-sulfamoylthiophene-3-carboxylate (IX; R1 =H; R=CH3) is refluxed for 20 hours in 150 ml of 1N methanolic sodium methylate solution. The methanol is evaporated, the residue taken up in water, and the aqueous phase extracted with methylene chloride and acidified with concentrated hydrochloric acid; the product precipitates as crystals. It may be recrystallized from water or ethanol.

Workup

  1. customThe methanol is evaporated
  2. extractionthe aqueous phase extracted with methylene chloride
  3. customthe product precipitates as crystals
  4. customIt may be recrystallized from water or ethanol

Sources & evidence

ORD record
ord-b62206d4007544b999d978bdea214581
Source dataset
uspto-grants-1977_06
Patent number
US04028373

Reaction notes

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