Ammonium Acetate → Methyl 4-(4-chlorophenyl)-2-oxo-4-oxazoline-5-propionate

HRID 567153Notes

Reaction equation

HRID 567153 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([CH:8]([O:15][C:16](OC2C=CC=CC=2)=[O:17])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=O)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:31]>C(O)(=O)C>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]2[NH:31][C:16](=[O:17])[O:15][C:8]=2[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 11068849Methyl 4-(4-chlorobenzoyl)-4-phenoxycarbonyloxybutyrate

Product 1

HCID 10956936Methyl 4-(4-chlorophenyl)-2-oxo-4-oxazoline-5-propionateYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of methyl 4-(4-chlorobenzoyl)-4-phenoxycarbonyloxybutyrate (61.2 g), ammonium acetate (62.2 g) and acetic acid (300 ml) was stirred under reflux for 1.5 hours. The reaction mixture was concentrated, water was added to the resulting residue, and the crystals thus precipitated were collected by filtration. These were recrystallized from methanol to give colorless needles of methyl 3-[4-(4-chlorophenyl)-2-oxo-4-oxazolin-5-yl]propionate (36.6 g, 79%). m.p. 147-148° C.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionwater was added to the resulting residue
  4. customthe crystals thus precipitated
  5. filtrationwere collected by filtration
  6. customThese were recrystallized from methanol

Sources & evidence

ORD record
ord-d9d6417e2df84f6483e9257224c39ee2
Source dataset
uspto-grants-2001_01
Patent number
US06177452B1

Reaction notes

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