Phosgene → 2-Ethyl-4-methyl-1,3-thiazole-5-carbonyl chloride

HRID 846289Notes

Reaction equation

HRID 846289 reaction equation
[CH2:1]([C:3]1[S:4][C:5]([C:9]([OH:11])=O)=[C:6]([CH3:8])[N:7]=1)[CH3:2].C(Cl)([Cl:14])=O>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[S:4][C:5]([C:9]([Cl:14])=[O:11])=[C:6]([CH3:8])[N:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 138352922-Ethyl-4-methyl-1,3-thiazole-5-carboxylic acid

Product 1

HCID 147162072-Ethyl-4-methyl-1,3-thiazole-5-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a similar apparatus to Example 1, 8.6 g (0.05 mole) of 2-ethyl-4methylthiazole-5carboxylic acid were suspended in 200 ml of toluene. Under heating and reflux, phosgene was blown at a rate of 350 ml/hr for 11 hours (0.17 mole). After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to obtain 9.3 g of 2-ethyl-4-methylthiazole-5-carboxylic acid chloride. Its purity and yield were 94.5% and 97.5%, respectively. NMR (δCDCl 3/TMS, ppm):1.36(3H,t,J=8Hz), 2.62(3H,s), 2.93(2H,q,J=8Hz).

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-3d9ec7f0af644de297a321643647d90f
Source dataset
uspto-grants-1992_08
Patent number
US05136042

Reaction notes

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