Dimethylformamide → 5-Chloro-3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde

HRID 441858Notes

Reaction equation

HRID 441858 reaction equation
O=P(Cl)(Cl)[Cl:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:17][C:16](=O)[N:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:14]=2)=[CH:9][CH:8]=1.[OH-].[Na+].CN(C)[CH:29]=[O:30]>>[Cl:3][C:16]1[N:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:14]=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=2)[C:17]=1[CH:29]=[O:30]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 102860883-(4-Chlorophenyl)-1-phenyl-2-pyrazolin-5-one

Product 1

HCID 214183605-Chloro-3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehydeYield 99%

Procedure

At 5° to 10° 284 g of phosphorus oxytrichloride are added dropwise during a period of 90 minutes to 270 g of dimethylformamide. Stirring is carried out for 30 minutes at 15° and then 100 g of 3-p-chlorophenyl-1-phenyl-2-pyrazoline-5-one are added. Heating is carried out for 1.5 hours at 50° and for 21 hours at 70°. The product is poured on to 2 kg of ice, the pH is adjusted to 3-4 with 20 % of sodium hydroxide and the precipitate is filtered off. 5-Chloro-3-p-chlorophenyl-1-phenyl-pyrazole-4-carboxaldehyde is obtained with a yield of 99 %; F 169.5°-171° (from acetone).

Workup

  1. temperatureHeating
  2. waitis carried out for 1.5 hours at 50° and for 21 hours at 70°
  3. filtrationthe precipitate is filtered off

Sources & evidence

ORD record
ord-642c912b8d1c4b37811aa5e3f1620f44
Source dataset
uspto-grants-1977_08
Patent number
US04042702

Reaction notes

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