Phosgene → 2-Methyl-1,3-thiazole-5-carbonyl chloride

HRID 846286Notes

Reaction equation

HRID 846286 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:7]([OH:9])=O)=[CH:5][N:6]=1.C(Cl)([Cl:12])=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[S:3][C:4]([C:7]([Cl:12])=[O:9])=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 988455-Thiazolecarboxylic acid, 2-methyl-

Product 1

HCID 147162052-Methyl-1,3-thiazole-5-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a similar apparatus to Example 1,5.7 g (0.04 mole) of 2-methylthiazole-5-carboxylic acid were suspended in 100 ml of toluene. Under heating and reflux, phosgene was blown at a rate of 390 ml/hr for 10 hours (0.17 mole). After completion of the blowing, stirring was continued for additional 2 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to obtain 5.7 g of 2-methylthiazole-5-carboxylic acid chloride. Its purity and yield were 95.0% and 95.0%, respectively. NMR (δCDCl 3/TMS, ppm): 2.79(3H,s).

Workup

  1. temperatureUnder heating
  2. temperaturereflux
  3. customAfter completion of the reaction
  4. filtrationthe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cf19454ede3b428887f59661dbab25c8
Source dataset
uspto-grants-1992_08
Patent number
US05136042

Reaction notes

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