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

HRID 846288Notes

Reaction equation

HRID 846288 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:9]([OH:11])=O)=[C:5]([CH2:7][CH3:8])[N:6]=1.C(Cl)([Cl:14])=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[S:3][C:4]([C:9]([Cl:14])=[O:11])=[C:5]([CH2:7][CH3:8])[N:6]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 146487654-Ethyl-2-methyl-1,3-thiazole-5-carboxylic acid

Product 1

HCID 147162064-Ethyl-2-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-methyl-4-ethylthiazole-5carboxylic acid were suspended in 200 ml of toluene. Under heating and reflux, phosgene was blown at a rate of 340 ml/hr for 12 hours (0.18 mole). After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to obtain 9.2 g of 2-methyl-4-ethylthiazole-5-carboxylic acid chloride. Its purity and yield were 96.0% and 96.6%, respectively. NMR (δCDCl 3/TMS, ppm): 1.25(3H,t,J=8Hz), 2.46(3H,s), 3.06(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-e2d15e34dcec416b81a39b76f1384b63
Source dataset
uspto-grants-1992_08
Patent number
US05136042

Reaction notes

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