Thionyl Chloride → HCID 53967044, compound

HRID 972361Notes

Reaction equation

HRID 972361 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9](O)=[O:10])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19].S(Cl)([Cl:22])=O>>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([Cl:22])=[O:10])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 21406751HCID 21406751, compound

Product 1

HCID 53967044HCID 53967044, compound

Procedure

A mixture of 2,2',4'-trifluoro-4-biphenylylacetic acid (3.6 g.) and thionyl chloride (15 ml.) was refluxed for 1 hour; excess thionyl chloride was removed and the residual acid chloride distilled at 141°-143° C./1.0 mm as a yellow oil, solidifying on cooling, (3.11 g.). Recrystallisation from 62-68 petroleum ether gave colourless needles of 2,2',4'-trifluoro-4-biphenylylacetyl chloride, m.p. 70°-73° C. 1 g. of this was dissolved in ether (10 ml.) and the solution added slowly to a stirred mixture of ammonia (SG=0.880; 5 ml.) and ether (25 ml.) at room temperature. After stirring for 15 minutes, the product was isolated in ether, washed, dried and evaporated. Recrystallization of the residue from methylene chloride/40-60 petroleum ether followed by a further crystallization from 100-120 petroleum ether gave colourless plates of 2,2',4'-trifluoro-4-biphenylylacetamide, m.p. 137°-140° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customexcess thionyl chloride was removed
  3. distillationthe residual acid chloride distilled at 141°-143° C./1.0 mm as a yellow oil
  4. temperatureon cooling
  5. customRecrystallisation from 62-68 petroleum ether

Sources & evidence

ORD record
ord-bf72e7b3911a4047afd22857a4c8b15e
Source dataset
uspto-grants-1977_10
Patent number
US04052514

Reaction notes

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