Diethyl Ether → HCID 22618414, compound

HRID 842142Notes

Reaction equation

HRID 842142 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[CH:17]=[C:16]([S:18][C:19]([F:22])([F:21])[F:20])[C:15]([CH:23]([OH:25])[CH3:24])=[N:14]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>ClCCl>[C:23]([C:15]1[C:16]([S:18][C:19]([F:20])([F:21])[F:22])=[CH:17][N:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:5][C:4]=2[Cl:12])[N:14]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 22618617HCID 22618617, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 22618414HCID 22618414, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-(1-hydroxyethyl)-4-trifluoromethylthiopyrazole (1.1 g) in dichloromethane (40 ml) was added pyridinium chlorochromate (0.62 g), and the mixture stirred at room temperature overnight. Ether (50 ml) was added and the mixture filtered on diatomaceous earth. Evaporation of the filtrate in vacuo gave a brown solid, which was triturated with hexane and filtered. The filtrate was evaporated in vacuo to give a yellow solid, which recrystallised from cyclohexane to give 3-acetyl-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole (0.4 g) in the form of a yellow solid, m.p. 89-91° C.

Workup

  1. filtrationthe mixture filtered on diatomaceous earth
  2. customEvaporation of the filtrate in vacuo
  3. customgave a brown solid, which
  4. customwas triturated with hexane
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo
  7. customto give a yellow solid, which
  8. customrecrystallised from cyclohexane

Sources & evidence

ORD record
ord-f245a451103340e2aaa7cee37d55a41a
Source dataset
uspto-grants-2002_04
Patent number
US06372774B1

Reaction notes

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