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

HRID 1862867Notes

Reaction equation

HRID 1862867 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-046b8c987d8b4174b10a77c0e3ac2d4d
Source dataset
uspto-grants-1979_09
Patent number
US04166816

Reaction notes

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