Ethanol → 3,4-Diphenylpyrazole

HRID 265412Notes

Reaction equation

HRID 265412 reaction equation
C([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)=O.O.[NH2:19][NH2:20].[CH2:21](O)C>>[C:12]1([C:11]2[C:9]([C:4]3[CH:3]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:21][NH:20][N:19]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 12414341HCID 12414341, compound

Product 1

HCID 3017433,4-DiphenylpyrazoleYield 57%

Conditions

Temperature
40 °C

Procedure

Formyldeoxybenzoin (10 g) was suspended in ethanol (50 ml) and hydrazine hydrate (5 ml) added giving an orange solution which warmed to 40° C. This solution was stirred at room temperature for 3 hours and the solvent evaporated. The resulting oil was taken up in dichloromethane and washed with dilute hydrochloric acid (pH 2) and water, dried over potassium carbonate and evaporated to an orange solid. This was boiled in ether, cooled and filtered giving 3,4-diphenylpyrazole (5.64 g, 57%) as pale yellow crystals, m.p. 155°-6° C.

Workup

  1. customgiving an orange solution which
  2. customthe solvent evaporated
  3. washwashed with dilute hydrochloric acid (pH 2) and water
  4. dry with materialdried over potassium carbonate
  5. customevaporated to an orange solid
  6. temperaturecooled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-b613d66b4b334b7ea92d915af2cddbbd
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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