Diethyl Ether → HCID 22618414, compound

HRID 975503Notes

Reaction equation

HRID 975503 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 (40ml) 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-8394d72ed3ed41a188c8cbf1fbe43ace
Source dataset
uspto-grants-1997_03
Patent number
US05608077

Reaction notes

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