Thiazolidinedione → 4-Chloro-2-oxo-2,3-dihydro-1,3-thiazole-5-carbaldehyde

HRID 1584024Notes

Reaction equation

[S:1]1[CH2:5][C:4](=O)[NH:3][C:2]1=[O:7].P(Cl)(Cl)([Cl:10])=O.CN(C)[CH:15]=[O:16]>>[Cl:10][C:4]1[NH:3][C:2](=[O:7])[S:1][C:5]=1[CH:15]=[O:16]

Participants

Reactant 3

HCID 5437Thiazolidinedione

HCID 6228Dimethylformamide

HCID 24813Phosphorus oxychloride

Product 1

HCID 121980294-Chloro-2-oxo-2,3-dihydro-1,3-thiazole-5-carbaldehydeYield 40%

Conditions

Temperature: 80 °C

Procedure

The reaction between 2,4-thiazolidinedione (III), dimethylformamide and phosphorus oxychloride is described in Khim. Geterotsikl. Soedin 1975, page 85 (English translation: Chem. Het. Comp. 1975, page 73). In this reaction, the three substances mentioned are, in an optimum molar ratio of 1:1.5:3, heated at 80° C. for 16 hours and at 115° to 130° C. for a short time and then hydrolyzed, whereupon 4-chloro-2,3-dihydro-2-oxo-5-thiazolecarboxaldehyde of the formula (I) ##STR2## is obtained in 40 to 60% yield.

Workup

customIn this reaction

Sources & evidence

ORD record: ord-6e7d502e616449cebea8842f82602338
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04555577

Reaction notes

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