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

HRID 867218Notes

Reaction equation

HRID 867218 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 mmol) [J. Org. Chem., 38, 3034 (1973)], thionyl chloride (5 ml) and methylene chloride (20 ml) is refluxed for 2.5 hours. After cooling to room temperature the solvent is removed in vacuo and resulting oil crystallizes on standing. The product is triturated with ether-hexane to give the title compound: 2.0 g mp 104°-112°.

Workup

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

Sources & evidence

ORD record
ord-e5be48a9a9b64d1e9275b4ced6c6741f
Source dataset
uspto-grants-1978_07
Patent number
US04103086

Reaction notes

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