Hydrochloric Acid → 3-Oxo-3-(thiophen-3-yl)propanenitrile
Reaction equation
N[C:2]([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)=[CH:3][C:4]#[N:5].Cl.C[OH:13]>>[O:13]=[C:2]([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)[CH2:3][C:4]#[N:5]Participants
4
Procedure
A 1.2 g. portion of β-amino-3-thiopheneacrylonitrile is added to 10 ml. of 1 N hydrochloric acid. A 40 ml. portion of methanol is added and the mixture is stirred for 3 hours. The mixture is evaporated in vacuo to a residue which is dissolved in 35 ml. of hot methanol and treated with charcoal. After cooling, petroleum ether is added, the mixture is filtered and the solid collected is discarded. The filtrate is allowed to evaporate and the residue is dissolved in 35 ml. of hot isopropanol and isoluble material filtered and discarded. The filtrate is cooled and the solid is collected giving the desired product as white plates, m.p. 87°-88° C.
Workup
- customThe mixture is evaporated in vacuo to a residue which
- dissolutionis dissolved in 35 ml
- additionof hot methanol and treated with charcoal
- temperatureAfter cooling
- additionpetroleum ether is added
- filtrationthe mixture is filtered
- customthe solid collected
- customto evaporate
- dissolutionthe residue is dissolved in 35 ml
- filtrationof hot isopropanol and isoluble material filtered
- temperatureThe filtrate is cooled
- customthe solid is collected
Sources & evidence
- ORD record
- ord-ab6a95c8eaad484e981a454159d657a7
- Source dataset
- uspto-grants-1980_02
- Patent number
- US04189436
Reaction notes
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