Water → alpha,alpha-Bis(4-chlorophenyl)-1H-pyrazole-4-methanol

HRID 64634Notes

Reaction equation

HRID 64634 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([C:10]2[CH:11]=[N:12]C=[N:14][CH:15]=2)[OH:9])=[CH:4][CH:3]=1.NN.O>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([C:10]2[CH:11]=[N:12][NH:14][CH:15]=2)[OH:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 161536LY 43578

Product 1

HCID 13672688alpha,alpha-Bis(4-chlorophenyl)-1H-pyrazole-4-methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The methiodide salt of α,α-bis(4-chlorophenyl)-pyrimidine-5-methanol (12.8 g) was heated to reflux with 3 g of anhydrous hydrazine in ethanol. The original slurry went into solution and then a precipitate formed, at which time 25 ml of water were added. The mixture was heated at reflux for 20 minutes, filtered hot, water was added and the mixture was extracted with ether. The ether was evaporated and the residue was crystallized from chloroform to provide the title product, m.p. 135°-137° C. The NMR and mass spectra were consistent with the desired structure.

Workup

  1. additionwere added
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 20 minutes
  4. filtrationfiltered hot
  5. additionwater was added
  6. extractionthe mixture was extracted with ether
  7. customThe ether was evaporated
  8. customthe residue was crystallized from chloroform

Sources & evidence

ORD record
ord-883462650c1c42c3bb7da08a9468e273
Source dataset
uspto-grants-1986_09
Patent number
US04609666

Reaction notes

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