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

HRID 846293Notes

Reaction equation

HRID 846293 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:7]([OH:9])=O)=[CH:5][N:6]=1.C1N2CCN(CC2)C1.C(Cl)([Cl:20])=O>C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[S:3][C:4]([C:7]([Cl:20])=[O:9])=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 9237DabcoHCID 988455-Thiazolecarboxylic acid, 2-methyl-

Product 1

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

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In a similar apparatus to Example 1, 10.0 g (0.07 mole) of 2-methylthiazole-5-carboxylic acid were suspended in 100 ml of xylene, followed by the addition of 0.03 g of triethylenediamine. Under heating and reflux, phosgene was blown at a rate of 930 ml/hr for 6 hours (0.25 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 10.5 g of 2-methylthiazole-5-carboxylic acid chloride. Its purity and yield were 96.0% and 92.8%, respectively.

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-04cabf7688ab499dbb6e43e16898db16
Source dataset
uspto-grants-1992_08
Patent number
US05136042

Reaction notes

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