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

HRID 2300661Notes

Reaction equation

HRID 2300661 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-6b04b6d85c6648668d09eec28bee17cd
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

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