Ammonia → HCID 14572471, compound

HRID 1973192Notes

Reaction equation

HRID 1973192 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9](OC)=[O:10])=[CH:7][CH:6]=1.[NH3:17]>CO>[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([NH2:17])=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 3710459HCID 3710459, compound

Product 1

HCID 14572471HCID 14572471, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-(2,2,2-trifluoroethoxy)-benzoate (3 g., 0.013 mole) in methanol (25 ml.) is cooled using a dry-ice acetone bath, and the solution is saturated with anhydrous ammonia, then heated in a pressure reactor at 110° for 10 hours. The methanolic solution is filtered and the filtrate is evaporated. The residue is chromatographed on neutral alumina and the early fractions which elute rapidly with ethyl acetate are discarded, methyl ethyl ketone fractions are discarded and methanol fractions finally give a tan solid when evaporated. When recrystallized from ethanol the white solid is found to be 4-(2,2,2-trifluoroethoxy)benzamide, m.p. 177°-178° C.

Workup

  1. temperatureheated in a pressure reactor at 110° for 10 hours
  2. filtrationThe methanolic solution is filtered
  3. customthe filtrate is evaporated
  4. customThe residue is chromatographed on neutral alumina
  5. washthe early fractions which elute rapidly with ethyl acetate
  6. custommethanol fractions finally give a tan solid when
  7. customevaporated
  8. customWhen recrystallized from ethanol the white solid

Sources & evidence

ORD record
ord-29225a772b794f9181cf4aba375d6ca7
Source dataset
uspto-grants-1976_12
Patent number
US03996280

Reaction notes

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