Phosgene → 4-Methyl-1,3-thiazole-5-carbonyl chloride

HRID 846294Notes

Reaction equation

HRID 846294 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[C:7]([OH:9])=O.CN(C)P(N(C)C)(N(C)C)=O.C(Cl)([Cl:23])=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[C:7]([Cl:23])=[O:9]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 12679HexamethylphosphoramideHCID 2098054-Methylthiazole-5-carboxylic acid

Product 1

HCID 124702104-Methyl-1,3-thiazole-5-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a similar apparatus to Example 1, 7.2 g (0.05 mole) of 4-methylthiazole-5-carboxylic acid were suspended in 100 ml of toluene, followed by the addition of 0.02 g of hexamethylphosphoramide Under heating and reflux, phosgene was blown at a rate of 1.2 l/hr for 2.5 hours (0.13 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 8.0 g of 4-methylthiazole-5-carboxylic acid chloride. Its purity and yield were 99.2% an d99.0%, respectively. NMR (δCDCl 3/TMS, ppm): 2.88(3H,s).

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-e7a317cabfec4a43b0afcd55b8491e56
Source dataset
uspto-grants-1992_08
Patent number
US05136042

Reaction notes

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