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

HRID 1112472Notes

Reaction equation

HRID 1112472 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°-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 etherhexane

Sources & evidence

ORD record
ord-bce8a6f76ffb405db7d42db0c3ef4f49
Source dataset
uspto-grants-1978_10
Patent number
US04122262

Reaction notes

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