Phenol → HCID 13282761, compound

HRID 746110Notes

Reaction equation

HRID 746110 reaction equation
Cl[C:2]1[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[C:16]1([OH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[O:22]([C:2]1[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 1235240Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

Product 1

HCID 13282761HCID 13282761, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5.2 g (0.02 mole) of ethyl 2-chloro-4-trifluoromethyl-5-thiazolecarboxylate, 1.88 g (0.02 mole) of phenol, 2.76 g (0.02 mole) of K2CO3 and 50 ml. of acetone was held at reflux for 3 days. Acetone was removed under reduced pressure. The residue was treated with water, extracted with ether. The ether solution was dried (MgSO4) and concentrated under reduced pressure. The residual solid was heated with hexane, cooled and filtered to give 4.8 g (76%) of the desired product, m.p. 52°-54° C.

Workup

  1. temperatureat reflux for 3 days
  2. customAcetone was removed under reduced pressure
  3. additionThe residue was treated with water
  4. extractionextracted with ether
  5. dry with materialThe ether solution was dried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. temperatureThe residual solid was heated with hexane
  8. temperaturecooled
  9. filtrationfiltered

Sources & evidence

ORD record
ord-a1617df515eb43b18fc78eb44320b04c
Source dataset
uspto-grants-1986_07
Patent number
US04602454

Reaction notes

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