Hydrochloric Acid → 2-(4-Fluorophenyl)-1-[4-(methylthio)phenyl]-4,4,4-trifluoro-1,3-butanedione

HRID 1609604Notes

Reaction equation

HRID 1609604 reaction equation
N[C:2]([C:21]([F:24])([F:23])[F:22])=[C:3]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:4]([C:6]1[CH:11]=[CH:10][C:9]([S:12][CH3:13])=[CH:8][CH:7]=1)=[O:5].Cl.CC[O:28]CC>>[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH:3]([C:2](=[O:28])[C:21]([F:24])([F:23])[F:22])[C:4]([C:6]2[CH:11]=[CH:10][C:9]([S:12][CH3:13])=[CH:8][CH:7]=2)=[O:5])=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 697263953-Amino-4,4,4-trifluoro-2-(4-fluorophenyl)-1-[4-(methylthio)phenyl]-2-buten-1-one

Product 1

HCID 193560322-(4-Fluorophenyl)-1-[4-(methylthio)phenyl]-4,4,4-trifluoro-1,3-butanedione

Procedure

A mixture of 4.0 g of product of step 1, 40 mL of ether, and 40 mL of 6N hydrochloric acid was stirred at room temperature for 4 days. The ether layer was dried over magnesium sulfate and concentrated in vacuo to give 4.0 g of crude 2-(4-fluorophenyl)-1-[4-(methylthio)phenyl]-4,4,4-trifluoro-1,3-butandione. A mixture of 0.22 g (0.59 mmol) of this product, 0.09 g of phenylhydrazine, and 10 mL of glacial acetic acid was heated at 80° C. for 18 hours and poured into water. The insoluble solid was purified by HPLC (10% ethyl acetate-hexane) to give 8 mg of 4-(4-fluorophenyl)-3-[4-(methylthio)phenyl]-1-phenyl-5-(trifluoromethyl)pyrazole and 140 mg of 4-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-1-phenyl-3-(trifluoromethyl)pyrazole.

Workup

  1. dry with materialThe ether layer was dried over magnesium sulfate
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28ac0f346b7341cba067a82c3baefec8
Source dataset
uspto-grants-1995_03
Patent number
US05401765

Reaction notes

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