Phenylhydrazine → HCID 59436173, compound

HRID 1407269Notes

Reaction equation

HRID 1407269 reaction equation
C[N:2]([CH:4]=[N:5][C:6]([C:8]1[C:13](=[O:14])[CH:12]=[CH:11][N:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[N:9]=1)=O)C.[C:25]1([NH:31]N)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)(=O)C>[C:25]1([N:31]2[C:6]([C:8]3[C:13](=[O:14])[CH:12]=[CH:11][N:10]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=4)[N:9]=3)=[N:5][CH:4]=[N:2]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 59436171HCID 59436171, compound

Product 1

HCID 59436173HCID 59436173, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A solution of N-[(dimethylamino)methylidene]-4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxamide (0.119 g, 0.35 mmol) in acetic acid (5.0 mL) was treated with phenyl hydrazine (0.070 mL, 0.71 mmol). The resulting solution was heated under microwave heating conditions at 120° C. for 10 min. After that time the reaction was cooled to room temperature and the crude product purified by flash column chromatography (silica gel, ethyl acetate to 85:15 ethyl acetate/methanol) to give a colorless solid that was recrystallized from ethyl acetate/hexanes to give 0.126 g (46%) of 3-(1-phenyl-1H-1,2,4-triazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one as colorless crystals.

Workup

  1. temperatureThe resulting solution was heated under microwave
  2. temperatureAfter that time the reaction was cooled to room temperature
  3. customthe crude product purified by flash column chromatography (silica gel, ethyl acetate to 85:15 ethyl acetate/methanol)
  4. customto give a colorless solid
  5. customthat was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e2205db0b43f4de58a66717af5758aab
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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