Ammonia → 2,2-Difluoro-2-phenylacetamide

HRID 1457209Notes

Reaction equation

HRID 1457209 reaction equation
[F:1][C:2]([F:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3](OCC)=[O:4].[NH3:15]>CCO>[F:1][C:2]([F:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([NH2:15])=[O:4]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10631860Ethyl 2,2-difluoro-2-phenylacetate

Product 1

HCID 2696562,2-Difluoro-2-phenylacetamideYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the title compound of Step (A) (6.00 g; 30 mmol) in 50 ml of EtOH was saturated with anhydrous NH3. An exothermic reaction was observed. After stirring the reaction mixture 60 hr at room temperature, the volatiles were removed in vacuo and the solid residue was taken up in a minimal amount of hot ethyl acetate. A small amount of insoluble material was filtered off and hexane was added to the filtrate until slightly turbid. After cooling to room temperature and standing several hr, the crystals were filtered and dried to afford 4.68 g (91%) of the title compound of this step as a colorless crystalline solid.

Workup

  1. customAn exothermic reaction
  2. customthe volatiles were removed in vacuo
  3. filtrationA small amount of insoluble material was filtered off
  4. additionhexane was added to the filtrate until slightly turbid
  5. temperatureAfter cooling to room temperature
  6. waitstanding several hr
  7. filtrationthe crystals were filtered
  8. customdried

Sources & evidence

ORD record
ord-f969fd42a4e149a1a52bb36191ea5073
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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