Ammonia → 6-methyl-6,7-dihydro-5H-thieno[3,2-c]pyridin-4-one
Reaction equation
[N:1]([CH:4]([CH3:11])[CH2:5][C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)=[C:2]=[O:3].N>C(Cl)Cl>[CH3:11][CH:4]1[NH:1][C:2](=[O:3])[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH2:5]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To PPA (15 ml) a solution of 2-(2-isocyanatopropyl)-thiophene in CH2Cl2 (15 ml) was added. The reaction mixture was stirred under reflux for 3 h, cooled, poured into ice and alkalified with concentrated ammonia. Then, the mixture was extracted with chloroform, dried over Na2SO4 and concentrated on rotary evaporator. The residue was purified by flash column chromatography on silica gel (eluent: chloroform/acetone—0→30%) to give 0.5 g of the target compound as a white solid.
Workup
- temperatureunder reflux for 3 h
- temperaturecooled
- additionpoured into ice
- extractionThen, the mixture was extracted with chloroform
- dry with materialdried over Na2SO4
- concentrationconcentrated on rotary evaporator
- customThe residue was purified by flash column chromatography on silica gel (eluent: chloroform/acetone—0→30%)
Sources & evidence
- ORD record
- ord-0b432daef3bb455abcf65a68ee96d7bd
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07947689B2
Reaction notes
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