Ammonia → 2-(4-nitrophenoxy)acetamide

HRID 1956424Notes

Reaction equation

HRID 1956424 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10](O)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[NH3:19]>C(O)C>[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([NH2:19])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 15720(4-Nitrophenoxy)acetic acidHCID 24386Thionyl Chloride

Product 1

HCID 6704702-(4-nitrophenoxy)acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Nitrophenoxyacetic acid (10.2 g) was added to thionyl chloride (50 ml) and the mixture was boiled under reflux for 1.5 hours. Excess thionyl chloride was distilled off and the residue was heated with toluene (2×50 ml) and the toluene removed by distillation to leave an oil which solidified on cooling. The acid chloride was added in portions to a stirred mixture of absolute ethanol (50 ml) and concentrated aqueous ammonia (50 ml, SG 0.880) at 10°-15° C. The mixture was stirred for 45 minutes at 10°-15° C. and then allowed to warm up to ambient temperature. The mixture was filtered to give 4-nitrophenoxyacetamide, m.p. 153°-155° C.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. distillationExcess thionyl chloride was distilled off
  3. temperaturethe residue was heated with toluene (2×50 ml)
  4. customthe toluene removed by distillation
  5. customto leave an oil which
  6. temperatureon cooling
  7. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-66bc2a0820c54ee4acbc9908b8b09f3c
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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