Thionyl Chloride → 2-Chloro-4-methylthiazole-5-carboxylic acid chloride

HRID 1111397Notes

Reaction equation

HRID 1111397 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:8]([OH:10])=O)=[C:5]([CH3:7])[N:6]=1.S(Cl)([Cl:13])=O>CN(C)C=O>[Cl:1][C:2]1[S:3][C:4]([C:8]([Cl:13])=[O:10])=[C:5]([CH3:7])[N:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 6669602-Chloro-4-methyl-1,3-thiazole-5-carboxylic acid

Product 1

HCID 135933932-Chloro-4-methylthiazole-5-carboxylic acid chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

8.8 g of 2-chloro-4-methylthiazole-5-carboxylic acid was suspended in 7 ml of thionyl chloride, and one drop of N,N-dimethylformamide was added. The mixture was heated under reflux for 1 hour, and then the excess of thionyl chloride was evaporated under reduced pressure Benzene (10 ml) was added, and the mixture was evaporated under reduced pressure. This procedure was repeated three times to give 9.7 g of 2-chloro-4-methylthiazole-5-carboxylic acid chloride which was used in the following reaction without purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customthe excess of thionyl chloride was evaporated under reduced pressure Benzene (10 ml)
  4. additionwas added
  5. customthe mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6dd3746899014e568f00fa2e2d74ee0e
Source dataset
uspto-grants-1990_12
Patent number
US04980363

Reaction notes

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