Tetrahydrofuran → 2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylic acid
Reaction equation
[CH3:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10]([O:12]CC)=[O:11])[NH:5][C:4]=2[C:3]=1[N:15]([CH3:24])[S:16]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)(=[O:18])=[O:17].O1CCCC1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10]([OH:12])=[O:11])[NH:5][C:4]=2[C:3]=1[N:15]([CH3:24])[S:16]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)(=[O:18])=[O:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a mixture of ethyl 2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylate (8.39 g), tetrahydrofuran (50 mL) and ethanol (50 mL) was added 8N aqueous sodium hydroxide solution (10 mL), and the mixture was stirred at 60° C. overnight. The reaction mixture was concentrated, 6N hydrochloric acid was added to the obtained residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. Crystallization from diethyl ether gave 2-methyl-3-[methyl(2-thienylsulfonyl)amino]-4H-thieno[3,2-b]pyrrole-5-carboxylic acid (7.07 g, yield 91%) as brown crystals.
Workup
- concentrationThe reaction mixture was concentrated
- addition6N hydrochloric acid was added to the obtained residue
- extractionthe mixture was extracted with ethyl acetate
- washThe ethyl acetate layer was washed with saturated brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customCrystallization from diethyl ether
Sources & evidence
- ORD record
- ord-e882d971e98d48fca68378e25c0152a7
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492405B2
Reaction notes
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