Ammonia → 3-Thiophenecarboxylic acid, 4-(aminosulfonyl)-, methyl ester
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>[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
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Methyl 4-(chlorosulfonyl)thiophene-3-carboxylate (5 g, 20.75 mmol) was dissolved in methylene chloride (50 mL), the solution was cooled to 0° C., and ammonia gas (1.1 g, 64.7 mmol) was introduced during 20 min. After a further 2 h of stirring, the reaction mixture was washed to neutrality with 10% aqueous hydrochloric acid and then with brine. After concentration os the solvent, crude methyl 4-sulfamoylthiophene-3-carboxylate was obtained which was recrystallized from ethanol to yield 2.7 g of methyl 4-sulfamoylthiophene-3-carboxylate. MS: 220 (M−1), 221.9 (M+1), 243.8 (M+Na).
Workup
- washthe reaction mixture was washed
- concentrationAfter concentration os the solvent
Sources & evidence
- ORD record
- ord-ebf3a682d9834c4781d1d1470699e25d
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07101880B2
Reaction notes
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