Hydrochloric Acid → 2-Sulfamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine
Reaction equation
[S:1]([C:5]1[S:16][C:8]2[CH2:9][N:10](C(=O)C)[CH2:11][CH2:12][C:7]=2[CH:6]=1)(=[O:4])(=[O:3])[NH2:2].Cl.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.CO>[OH-].[Na+]>[S:1]([C:5]1[S:16][C:8]2[CH2:9][NH:10][CH2:11][CH2:12][C:7]=2[CH:6]=1)(=[O:3])(=[O:4])[NH2:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A suspension of 2-sulfamoyl-6-acetyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (9.61 g, 37 mmol) in 20% sodium hydroxide solution (75 ml) was warmed at 80° C. for 3 hours. The resultant clear solution was cooled, acidified with concentrated hydrochloric acid, and then made basic with saturated sodium carbonate solution. The product was isolated by exhaustive extraction into ethyl acetate/methanol. The dried solution was evaporated to give 7.36 g (91% yield) of product. Recrystallization from ethyl acetate/methanol gave pure product; m.p. 172°-175° C.
Workup
- temperatureThe resultant clear solution was cooled
- customThe dried solution was evaporated
Sources & evidence
- ORD record
- ord-c67af48a0b7f4bc989bceca52911f178
- Source dataset
- uspto-grants-1988_03
- Patent number
- US04731368
Reaction notes
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