Dimethylformamide → 1-(4-Chlorophenyl)-3-(5-nitrofuran-2-yl)-1H-pyrazole-4-carbaldehyde

HRID 839204Notes

Reaction equation

HRID 839204 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][N:19]=[C:20]([C:22]2[O:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)[CH3:21])=[CH:14][CH:13]=1.N1C=C(C=[N+](C)C)[CH:32]=N1>O>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH:32]=[C:21]([CH:8]=[O:9])[C:20]([C:22]3[O:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=3)=[N:19]2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 203259884-PyrazolylmethylenedimethylammoniumHCID 858763735-Nitro-2-acetylfuran-p-chlorophenylhydrazone

Product 1

HCID 203261831-(4-Chlorophenyl)-3-(5-nitrofuran-2-yl)-1H-pyrazole-4-carbaldehydeYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 37 g of phosphorus oxychloride dropwise to 153 ml of dimethylformamide at from 10° to 20° C. Stir the thus-obtained admixture for 30 minutes at room temperature before adding 18.3 g of 5-nitro-2-acetylfuran-p-chlorophenylhydrazone in portions, thus causing the temperature to rise to 40° C. Stir for 4 additional hours at 40° C and then pour the solution containing the 4-pyrazolylmethylenedimethylammonium salt onto 1 kg of ice and water. Heat the so-cooled solution for 1 hour at 40° C, and then (vacuum) filter it at room temperature. Wash filter residue with water to obtain a 92% yield of 1-(p-chlorophenyl)-3-(5-nitro-2-furyl)pyrazole-4-carboxaldehyde [m.p. 192° to 193° C (from toluene)].

Workup

  1. customto rise to 40° C
  2. stirringStir for 4 additional hours at 40° C
  3. additionpour the solution
  4. temperatureHeat the so-cooled solution for 1 hour at 40° C
  5. filtration(vacuum) filter it at room temperature
  6. washWash
  7. filtrationfilter residue with water

Sources & evidence

ORD record
ord-88efe5b04a444e0ab1175ef4e510b34c
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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