4-Methoxyphenylhydrazine hydrochloride → HCID 9974904, compound

HRID 1379094Notes

Reaction equation

HRID 1379094 reaction equation
[F:1][CH:2]([F:16])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1)=O.Cl.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][NH2:27])=[CH:22][CH:21]=1>C(O)(=O)C>[F:1][CH:2]([F:16])[C:3]1[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=2)[N:26]([C:23]2[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)[N:27]=1

Participants

4

Reactant 2

HCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 10634032HCID 10634032, compound

Product 1

HCID 9974904HCID 9974904, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4,4-difluoro-1-[4-(methylthio)phenyl]-butane-1,3-dione (2.4 g) and 4-methoxyphenylhydrazine hydrochloride (1.9 g) in acetic acid (10 ml) was stirred at 100° C. for 1 hour. The solvent was evaporated and the residue was purified by column chromatography on silica gel (30 g) eluting with toluene. The purified oily product was crystallized from ethanol to give crystals of 3-(difluoromethyl)-1-(4-methoxyphenyl)-5-[4-(methylthio)phenyl]pyrazole (2.5 g).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography on silica gel (30 g)
  3. washeluting with toluene
  4. customThe purified oily product was crystallized from ethanol

Sources & evidence

ORD record
ord-cf6daf4c129a451ebac5e3f93455c448
Source dataset
uspto-grants-1997_09
Patent number
US05670533

Reaction notes

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