Hydrochloric Acid → 3-Oxo-3-(thiophen-3-yl)propanenitrile

HRID 1702968Notes

Reaction equation

HRID 1702968 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

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 54536012beta-Amino-3-thiopheneacrylonitrile

Product 1

HCID 27400753-Oxo-3-(thiophen-3-yl)propanenitrile

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 collected solid is discarded. The filtrate is evaporated and the residue is dissolved in 35 ml. of hot isopropanol and the insoluble material is filtered and discarded. The filtrate is cooled and the solid is collected giving the desired products as white plates, mp. 87°-88° C.

Workup

  1. customThe mixture is evaporated in vacuo to a residue which
  2. dissolutionis dissolved in 35 ml
  3. additionof hot methanol and treated with charcoal
  4. temperatureAfter cooling
  5. additionpetroleum ether is added
  6. filtrationthe mixture is filtered
  7. customThe filtrate is evaporated
  8. dissolutionthe residue is dissolved in 35 ml
  9. filtrationof hot isopropanol and the insoluble material is filtered
  10. temperatureThe filtrate is cooled
  11. customthe solid is collected

Sources & evidence

ORD record
ord-af28c428355f491bb51822c43707b914
Source dataset
uspto-grants-1982_09
Patent number
US04350689

Reaction notes

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