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

HRID 846295Notes

Reaction equation

HRID 846295 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.CN(C)C=O.C(Cl)([Cl:19])=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[S:3][C:4]([C:9]([Cl:19])=[O:11])=[C:5]([CH2:7][CH3:8])[N:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 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, 18.8 g (0.11 mole) of 2-methyl-4ethylthiazole-5carboxylic acid were suspended in 150 ml of toluene, followed by the addition of 0.1 g of N,N-dimethylformamide. Under heating and reflux, phosgene was blown at a rate of 1.5 l/hr for 4 hours (0.27 mole). After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to obtain 20.3 g of 2-methyl-4-ethylthiazole-5-carboxylic acid chloride. Its purity and yield were 98.0% and 97.5%, 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-fd4a84f32daa4ae9bd311c87f4646e9e
Source dataset
uspto-grants-1992_08
Patent number
US05136042

Reaction notes

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