Thionyl Chloride → 3(2H)-Oxazoleacetyl chloride, 2-oxo-4,5-diphenyl-

HRID 2050394Notes

Reaction equation

HRID 2050394 reaction equation
[C:1]1([C:7]2[N:8]([CH2:19][C:20]([OH:22])=O)[C:9](=[O:18])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:25])=O>C(Cl)Cl>[C:1]1([C:7]2[N:8]([CH2:19][C:20]([Cl:25])=[O:22])[C:9](=[O:18])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 104472003(2H)-Oxazoleacetic acid, 2-oxo-4,5-diphenyl-

Product 1

HCID 106389553(2H)-Oxazoleacetyl chloride, 2-oxo-4,5-diphenyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4,5-diphenyl-2-oxo-4-oxazolin-3-ylacetic acid (2.1 g, 7.1 mmole)[J. Org. Chem., 38, 3034 (1973)], 5 ml of thionyl chloride and 20 ml of methylene chloride is refluxed for 2.5 hours. After cooling to room temperature the solvent is removed in vacuo and the resulting oil crystallizes on standing. The product is triturated with ether-hexane to give 4,5-diphenyl-2-oxo-4-oxazolin-3-ylacetic acid chloride, mp 104°-112°.

Workup

  1. temperatureis refluxed for 2.5 hours
  2. customis removed in vacuo
  3. customthe resulting oil crystallizes on standing
  4. customThe product is triturated with ether-hexane

Sources & evidence

ORD record
ord-b5785899027b4e6987c2943e1db90c92
Source dataset
uspto-grants-1980_04
Patent number
US04200572

Reaction notes

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