Tetrahydrofuran → N-Methyl-N-[2-(1,3,4-thiadiazol-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamide
Reaction equation
[CH3:1][N:2]([S:22]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)(=[O:24])=[O:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:16][C:15](C(OCC)=O)=[N:14][N:13]=1)=[CH:8]2.[OH-].[Na+].O1CCCC1>CO>[CH3:1][N:2]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:16][CH:15]=[N:14][N:13]=1)=[CH:8]2)[S:22]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)(=[O:24])=[O:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of ethyl 5-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3,4-thiadiazole-2-carboxylate (0.20 g), 8N aqueous sodium hydroxide solution (0.14 mL), tetrahydrofuran (6 mL) and methanol (6 mL) was stirred at 50° C. for 2 hr. The reaction mixture was concentrated, and water was added to the residue. The mixture was acidified with 10% aqueous citric acid solution, and the resulting crystals were filtrated, washed with water and dried. The obtained crystals were dissolved in tetrahydrofuran, treated with activated carbon, and concentrated to give the title compound (0.13 g, yield 78%) as yellow crystals. melting point 270-271° C.
Workup
- concentrationThe reaction mixture was concentrated
- additionwater was added to the residue
- filtrationthe resulting crystals were filtrated
- washwashed with water
- customdried
- dissolutionThe obtained crystals were dissolved in tetrahydrofuran
- additiontreated with activated carbon
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a58cb7ea32024f4584f9445846fd77f2
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957070B2
Reaction notes
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