Phosphorus oxychloride → TA 1801

HRID 235863Notes

Reaction equation

HRID 235863 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][CH:9]([C:16]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)=[O:17])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]2[O:17][C:16]([C:18]3[O:19][CH:20]=[CH:21][CH:22]=3)=[C:9]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 13361429HCID 13361429, compound

Product 1

HCID 139577TA 1801Yield 85.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

37 g of ethyl 3-(4-chlorobenzoylamino)-3-(2-furylcarbonyl)propionate are dissolved in 150 ml of chloroform. 64.9 g of phosphorus oxychloride are added dropwise to the solution at room temperature, and the mixture is refluxed at 60° to 70° C. for 8 hours under stirring. After the reaction is completed, the mixture is poured into ice-water. The aqueous mixture is neutrallized with sodium bicarbonate and then extracted with ethyl acetate. The extract is washed with water, dried, treated with activated charcoal and then evaporated under reduced pressure to remove solvent. The residue is crystallized with diisopropyl ether, and then recrystallized from ethanol. 30 g of ethyl 2-[2-(4-chlorophenyl)-5-(2-furyl)-4-oxazolyl]acetate are thereby obtained. Yield: 85.5%

Workup

  1. temperaturethe mixture is refluxed at 60° to 70° C. for 8 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. additiontreated with activated charcoal
  6. customevaporated under reduced pressure
  7. customto remove solvent
  8. customThe residue is crystallized with diisopropyl ether
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-43aeb4c8dde84cd29f317907dd31ee0d
Source dataset
uspto-grants-1987_02
Patent number
US04642313

Reaction notes

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