Methyl 3-(aminosulfonyl)-2-thiophenecarboxylate → 2H,3H-1lambda6-thieno[2,3-d][1,2]thiazole-1,1,3-trione

HRID 436832

Reaction equation

HRID 436832 reaction equation
[S:1]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[C:10]([O:12]C)=O)(=[O:4])(=[O:3])[NH2:2]>C[O-].[Na+]>[O:12]=[C:10]1[C:6]2[S:7][CH:8]=[CH:9][C:5]=2[S:1](=[O:4])(=[O:3])[NH:2]1

Participants

3

Reactant 1

HCID 101012Methyl 3-(aminosulfonyl)-2-thiophenecarboxylate

Product 1

HCID 140865502H,3H-1lambda6-thieno[2,3-d][1,2]thiazole-1,1,3-trione

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

32 g (0.145 mole) of methyl 3-sulfamoylthiophene-2-carboxylate (IX) in 145 ml of 1N methanolic sodium methylate solution is refluxed for 18 hours. The methanol is then evaporated off, the residue is taken up in water and a small amount of sodium bicarbonate, and the aqueous phase is extracted with methylene chloride and acidified with concentrated hydrochloric acid, whereupon the product precipitates as crystals which can be reprecipitated from water or ethanol.

Workup

  1. customThe methanol is then evaporated off
  2. extractiona small amount of sodium bicarbonate, and the aqueous phase is extracted with methylene chloride
  3. customprecipitates as crystals which
  4. customcan be reprecipitated from water or ethanol

Sources & evidence

ORD record
ord-a1ab9e7cc2c4413ba4fb6912a1c95fbe
Source dataset
uspto-grants-1977_06
Patent number
US04028373

Linked notes

Loading…