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

HRID 846296Notes

Reaction equation

HRID 846296 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].CN(C)C(=O)C.C(Cl)([Cl:20])=O>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[S:4][C:5]([C:9]([Cl:20])=[O:11])=[C:6]([CH3:8])[N:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 31374DimethylacetamideHCID 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, 15.0 g (0.09 mole) of 2-ethyl-4-methylthiazole-5-carboxylic acid were suspended in 150 ml of toluene, followed by the addition of 0.1 g of N,N-dimethylacetamide. Under heating and reflux, phosgene was blown at a rate of 1.5 l/hr for 3.5 hours (0.23 mole). After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to obtain 16.1 g of 2-ethyl-4-methylthiazole-5-carboxylic acid chloride. Its purity and yield were 98.2% and 96.9%, 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-dbf1dd08c8d1453fb60aa7594a78fb57
Source dataset
uspto-grants-1992_08
Patent number
US05136042

Reaction notes

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