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

HRID 1030110Notes

Reaction equation

HRID 1030110 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
  4. additionBenzene (10 ml) was added
  5. customthe mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9526b21a2f9149768b8fd585de14c167
Source dataset
uspto-grants-1992_04
Patent number
US05104886

Reaction notes

Loading…