Hexane → 3-(m-Trifluoromethylbenzylmercapto)-2,5-pyridine-dicarboxylic acid dimethyl ester
Reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][SH:7].[H-].[Na+].CCCCCC.[CH3:21][O:22][C:23]([C:25]1[C:30]([N+]([O-])=O)=[CH:29][C:28]([C:34]([O:36][CH3:37])=[O:35])=[CH:27][N:26]=1)=[O:24]>CN(C)C=O.O.C(O)(=O)C>[CH3:21][O:22][C:23]([C:25]1[C:30]([S:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:4]=2)=[CH:29][C:28]([C:34]([O:36][CH3:37])=[O:35])=[CH:27][N:26]=1)=[O:24]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
The solution of 4.6 g of m-trifluoromethylbenzylmercaptan in 30 ml of dimethylformamide is added to the slurry of 1.08 g of 50% sodium hydride in mineral oil (washed 2 times with hexane), under nitrogen while stirring at room temperature. After several minutes, a clear yellow solution is obtained, which is combined with that of 5.0 g of 3-nitro-2,5-pyridinedicarboxylic acid dimethyl ester in 50 ml of dimethylformamide. The mixture is warmed on the steam bath for 30 minutes at 90° and stirred at room temperature overnight. It is acidified with 2 ml of acetic acid and diluted to 400 ml with a mixture of ice and water. The precipitate formed is collected and recrystallized from methanol-diethyl ether (1:1), to yield the 3-(m-trifluoromethylbenzylmercapto)-2,5-pyridine-dicarboxylic acid dimethyl ester melting at 102°-106°.
Workup
- waitAfter several minutes
- customa clear yellow solution is obtained
- temperatureThe mixture is warmed on the steam bath for 30 minutes at 90°
- stirringstirred at room temperature overnight
- customThe precipitate formed
- customis collected
- customrecrystallized from methanol-diethyl ether (1:1)
Sources & evidence
- ORD record
- ord-efd756ed420344f197f24e94481a5b3d
- Source dataset
- uspto-grants-1981_04
- Patent number
- US04260620
Reaction notes
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