Ammonia → 3-Thiophenecarboxylic acid, 4-(aminosulfonyl)-, methyl ester

HRID 436828Notes

Reaction equation

HRID 436828 reaction equation
Cl[S:2]([C:5]1[C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][S:8][CH:9]=1)(=[O:4])=[O:3].[NH3:14]>C(Cl)(Cl)Cl>[S:2]([C:5]1[C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][S:8][CH:9]=1)(=[O:4])(=[O:3])[NH2:14]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 12593671Methyl 4-(chlorosulfonyl)thiophene-3-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

39.9 g (0.166 mole) of methyl 4-chlorosulfonylthiophene-3-carboxylate (VIII) is dissolved in 400 ml of absolute chloroform; ammonia is passed in at room temperature until the mixture has an alkaline reaction. After the mixture has been stirred for a further 3 hours (care being taken that the solution remains alkaline) it is extracted with water and the organic phase is dried and evaporated. The crystalline residue can be recrystallized from ethanol; however, for further use, digestion with ether is sufficient.

Workup

  1. customis passed in at room temperature until the mixture
  2. customan alkaline reaction
  3. extractionis extracted with water
  4. customthe organic phase is dried
  5. customevaporated
  6. customThe crystalline residue can be recrystallized from ethanol

Sources & evidence

ORD record
ord-ea5cf465562c4a609d34e2c35fc2658b
Source dataset
uspto-grants-1977_06
Patent number
US04028373

Reaction notes

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