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

HRID 1448860Notes

Reaction equation

HRID 1448860 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 etherhexane to give 4,5-diphenyl-2-oxo-4-oxazolin-3-ylacetic acid chloride; 2.0 g mp 104°-12°.

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 etherhexane

Sources & evidence

ORD record
ord-3808a2656cd949ccbcbc4daafa09c9f5
Source dataset
uspto-grants-1980_02
Patent number
US04187375

Reaction notes

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