N,N-Diethylaniline → Acetonitrile, [(4-chloro-6-phenyl-2-pyrimidinyl)thio]-
Reaction equation
C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)([Cl:14])=O.O[C:18]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:21]=[C:20]([S:30][CH2:31][C:32]([NH2:34])=O)[N:19]=1>>[Cl:14][C:18]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:21]=[C:20]([S:30][CH2:31][C:32]#[N:34])[N:19]=1Participants
Procedure
To a solution of 14.9 g. (0.1 mole) of N,N-diethylaniline in 400 ml. of phosphorus oxychloride was added 26.1 g. (0.1 mole) of 2-(4-hydroxy-6-phenyl-2-pyrimidinylthio)acetamide. After being heated under reflux for one hour the phosphorus oxychloride was removed in a rotary evaporator. The residue was poured into 1000 ml. of ice-water and the precipitate was collected by filtration. The filter cake was triturated with 250 ml. of acetone with the insoluble material being removed by filtration. Dilution of filtrate with 250 ml. of water afforded a solid which was collected and recrystallized from ethyl acetate-petroleum ether to give 7 g. of material. A second recrystallization from ethyl acetate-heptane yielded the analytical sample, mp. 136°-141°.
Workup
- temperatureAfter being heated
- customwas removed in a rotary evaporator
- additionThe residue was poured into 1000 ml
- filtrationof ice-water and the precipitate was collected by filtration
- customThe filter cake was triturated with 250 ml
- customof acetone with the insoluble material being removed by filtration
- customof water afforded a solid which
- customwas collected
- customrecrystallized from ethyl acetate-petroleum ether
- customto give 7 g
- customA second recrystallization from ethyl acetate-heptane
- customyielded the analytical sample, mp. 136°-141°
Sources & evidence
- ORD record
- ord-7592b72461d245ae8be11e9bddcea449
- Source dataset
- uspto-grants-1976_04
- Patent number
- US03950339
Reaction notes
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