Reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:11])[CH2:8][C:9]#[N:10].C(N(CC)CC)C.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1>C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=[O:11])[CH:8]([C:28](=[O:29])[NH:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][CH3:19])=[CH:26][CH:25]=1)[C:9]#[N:10]Participants
5
Procedure
The suspension of 2.0 g of the 1-methyl-β-oxo-2-pyrrolpropionitrile in 50 ml of toluene and 1.6 g of triethylamine is treated with 2.1 g of p-methoxyphenylisocyanate. The mixture is warmed gently until all is dissolved and allowed to stand overnight at room temperature. It is evaporated, the residue is taken up in methanol and combined with 10 ml of 10% aqueous sodium hydroxide and 250 ml of water. The alkaline solution is filtered, acidified with 5 N hydrochloric acid and the precipitate formed collected. It is washed with water, dried, triturated with warm methanol-ethyl acetate, and recrystallized from ethyl acetate, to yield the 1-methyl-β-oxo-α-(p-methoxyphenylcarbamoyl)-2-pyrrolpropionitrile melting at 192°-193°.
Workup
- temperatureThe mixture is warmed gently until
- dissolutionall is dissolved
- customIt is evaporated
- filtrationThe alkaline solution is filtered
- customthe precipitate formed
- customcollected
- washIt is washed with water
- customdried
- customtriturated with warm methanol-ethyl acetate
- customrecrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-bd67a2403f5947ea99ebdfd823a2528c
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04256759
Linked notes
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