2-[2-(5-Chloro-2-methoxybenzoylamino)ethyl]-5-sulfamoylthiophene → 2-[2-(5-Chloro-2-methoxybenzoylamino)ethyl]-5-(amino-carbonylaminosulfonyl)thiophene
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[S:13][C:14]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:15][CH:16]=1)=[O:8].[O:24]([C:26]#[N:27])[K]>C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[S:13][C:14]([S:17]([NH:18][C:26]([NH2:27])=[O:24])(=[O:19])=[O:20])=[CH:15][CH:16]=1)=[O:8]Participants
4
Procedure
299 mg (0.8 mmol of 2-[2-(5-chloro-2-methoxybenzoylamino)ethyl]-5-sulfamoylthiophene were treated with 448 mg of KOCN and 0.6 ml of triethylamine, and the mixture was then heated to reflux for 4 h. The cooled solution was filtered and evaporated to dryness. The residue was stirred with 40 ml of H2O, 25 ml of triethylamine and 25 ml of ethyl acetate. The organic phase was extracted 3 times with water/1% triethylamine. The combined aqueous phases were acidified with 2N hydrochloric acid. The precipitate formed was stirred in an ice bath for 3 hours and filtered off with suction.
Workup
- temperaturethe mixture was then heated
- temperatureto reflux for 4 h
- filtrationThe cooled solution was filtered
- customevaporated to dryness
- extractionThe organic phase was extracted 3 times with water/1% triethylamine
- customThe precipitate formed
- stirringwas stirred in an ice bath for 3 hours
- filtrationfiltered off with suction
Sources & evidence
- ORD record
- ord-27f7c6d0b37b4d85b7687858dc855a77
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05792788
Reaction notes
Loading…