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

HRID 1733304Notes

Reaction equation

HRID 1733304 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 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

  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 solid collected
  8. customto evaporate
  9. dissolutionthe residue is dissolved in 35 ml
  10. filtrationof hot isopropanol and isoluble material filtered
  11. temperatureis cooled
  12. customthe solid is collected

Sources & evidence

ORD record
ord-3bc6011f6acb4146adb1f9389d601cef
Source dataset
uspto-grants-1980_12
Patent number
US04241077

Reaction notes

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