Diphosgene → HCID 10998791, compound

HRID 846291Notes

Reaction equation

HRID 846291 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[S:4][C:5]([C:9](O)=[O:10])=[C:6]([CH3:8])[N:7]=1.[Cl:14]C(OC(Cl)(Cl)Cl)=O>ClC1C=CC=CC=1.N1C=CC=CC=1>[F:1][C:2]([F:13])([F:12])[C:3]1[S:4][C:5]([C:9]([Cl:14])=[O:10])=[C:6]([CH3:8])[N:7]=1

Participants

5

Reactant 2

HCID 10426DiphosgeneHCID 108999004-methyl-2-(trifluoromethyl)-1,3-thiazole-5-carboxylic acid

Product 1

HCID 10998791HCID 10998791, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 7964ChlorobenzeneSolvent

Procedure

In a similar apparatus to Example 1, 4.2 g (0.02 mole) of 2-trifluoromethyl-4-methylthiazole-5-carboxylic acid were suspended in 100 ml of chlorobenzene, followed by the addition of 0.04 g of pyridine. Under heating and reflux, 9.9 g (0.05 mole) of trichloromethyl chloroformate were added dropwise over 5 hours. After completion of the dropwise addition, stirring was continued for additional 2 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to obtain 4.5 g of 2-trifluoromethyl-4-methylthiazole-5-carboxylic acid chloride. Its purity and yield were 98.7% and 98.0%, respectively.

Workup

  1. temperatureUnder heating
  2. temperaturereflux
  3. additionAfter completion of the dropwise addition
  4. customAfter completion of the reaction
  5. filtrationthe reaction mixture was filtered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2bdc6714dcb7439ba6c6637e0ccccbfb
Source dataset
uspto-grants-1992_08
Patent number
US05136042

Reaction notes

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