Ammonium Acetate → HCID 54285037, compound

HRID 2255224Notes

Reaction equation

HRID 2255224 reaction equation
[C:1]([O:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=O)(=O)[CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C([O-])(=O)C.[NH4+:25]>C(O)(=O)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[N:25]=[C:1]([CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[O:10][CH:11]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 539218831-[2-(4-Chlorophenyl)-2-oxoethyl] 4-ethyl butanedioate

Product 1

HCID 54285037HCID 54285037, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-(4-chlorophenyl)-2-oxoethyl ethyl succinate (7.6 g), ammonium acetate (9.8 g) and acetic acid (80 ml) was stirred for an hour at 110° C. and refluxed for 2 hours. The solvent was distilled off. The residue was diluted with water, made basic by addition of aqueous sodium hydrogen carbonate solution and then extracted with ethyl acetate. The ethyl acetate layer was washed with water, and dried over MgSO4. After removal of the solvent, the oily residue was subjected to a silica gel column chromatography. Crystals of ethyl 4-(4-chlorophenyl)-2-oxazolepropionate (2.23 g, 31%) were obtained from the fraction eluted with ethyl acetate-hexane (1:3, V/V). Recrystallization from ethyl acetate-hexane gave colorless plate crystals of mp 65°-66° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. distillationThe solvent was distilled off
  3. additionThe residue was diluted with water
  4. additionmade basic by addition of aqueous sodium hydrogen carbonate solution
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried over MgSO4
  8. customAfter removal of the solvent

Sources & evidence

ORD record
ord-cc5d6de01dda4a978ec8b64e28130afa
Source dataset
uspto-grants-1993_08
Patent number
US05239080

Reaction notes

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