Thionyl Chloride → HCID 87948105, compound

HRID 842044Notes

Reaction equation

HRID 842044 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[S:4][C:5]([C:12](O)=[O:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1.S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl.CN(C)C=O>[F:1][C:2]([F:16])([F:15])[C:3]1[S:4][C:5]([C:12]([Cl:19])=[O:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 184654872,4-Bis(trifluoromethyl)-5-thiazolecarboxylic acid

Product 1

HCID 87948105HCID 87948105, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To a 500 mL 1-neck RBF under N2 was added 2,4-bis-trifluoromethyl-thiazole-5-carboxylic acid (31.5 g, 1.0 equiv., 0.119 moles) in 25 mL chloroform and 1 mL dimethylformamide (DMF). To this solution was added thionyl chloride (28.3 g, 2.0 equiv., 0.24 moles). The reaction was then heated at reflux for 6 hours. The reaction was cooled to room temperature and concentrated by rotary evaporation at 30° C. to remove solvent. Chloroform was added, 3×25 mL portions, concentrating by rotary evaporation each time, to give 29.8 g (88.4% yield) product as a brown oil.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureat reflux for 6 hours
  3. concentrationconcentrated by rotary evaporation at 30° C.
  4. customto remove solvent
  5. additionChloroform was added
  6. concentration3×25 mL portions, concentrating by rotary evaporation each time

Sources & evidence

ORD record
ord-3bcbdb4c2fb04e79b090387aa8897f3b
Source dataset
uspto-grants-2002_04
Patent number
US06372769B1

Reaction notes

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