Thionyl Chloride → 2-Oxo-2,3-dihydro-1,3-thiazole-4-carbonyl chloride

HRID 1604978Notes

Reaction equation

HRID 1604978 reaction equation
[C:1]([C:4]1[NH:5][C:6](=[O:9])[S:7][CH:8]=1)(O)=[O:2].S(Cl)([Cl:12])=O>>[Cl:12][C:1]([C:4]1[NH:5][C:6](=[O:9])[S:7][CH:8]=1)=[O:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 205501812-Oxo-2,3-dihydro-1,3-thiazole-4-carboxylic acid

Product 1

HCID 215482312-Oxo-2,3-dihydro-1,3-thiazole-4-carbonyl chloride

Procedure

A mixture of 29 g of 4-carboxy-4-thiazoline-2-one [Enlenmeyer et al, Helv., Chim. Acta., Vol. 27 (1944), p.1432-6] and 200 ml of thionyl chloride was refluxed for 24 hours and was then cooled. The mixture was vacuum filtered to obtain 21 g of 4-chloroformyl-4-thiazoline-2-one melting at 184°C.

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperaturewas then cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-12e104f2cab947bfbcd82d04910d91a4
Source dataset
uspto-grants-1976_04
Patent number
US03948925

Reaction notes

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