Ammonium Acetate → 4-(4-Trifluoromethylphenyl)-2-oxazolone

HRID 395670Notes

Reaction equation

HRID 395670 reaction equation
[C:1](=[O:23])(OC1C=CC=CC=1)[O:2][CH2:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1.C([O-])(=O)C.[NH4+:28]>C(O)(=O)C>[F:12][C:11]([F:14])([F:13])[C:8]1[CH:9]=[CH:10][C:5]([C:4]2[NH:28][C:1](=[O:23])[O:2][CH:3]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 129929622-Oxo-2-(4-trifluoromethylphenyl)ethyl phenyl carbonate

Product 1

HCID 129929584-(4-Trifluoromethylphenyl)-2-oxazoloneYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-oxo-2-(4-trifluoromethylphenyl)ethyl phenyl carbonate (18.0 g), ammonium acetate (20 g) and acetic acid (100 ml) was stirred with heating under reflux for 1 hour. The reaction mixture was concentrated, and poured into ice water (200 ml). The solid precipitates were filtered, washed with water, and air-dried to give crystals of 4-(4-trifluoromethylphenyl)-2-oxazolone (10.8 g, 85%). Melting point decomposed at 250° C. or more.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hour
  3. concentrationThe reaction mixture was concentrated
  4. additionpoured into ice water (200 ml)
  5. customThe solid precipitates
  6. filtrationwere filtered
  7. washwashed with water
  8. customair-dried

Sources & evidence

ORD record
ord-56de366f4d664992af77b4b30182fa11
Source dataset
uspto-grants-2003_08
Patent number
US06605629B1

Reaction notes

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