Dimethylformamide → 3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde

HRID 839201Notes

Reaction equation

HRID 839201 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[C:11]1([NH:17][N:18]=[C:19]([C:21]2[O:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)[CH3:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1C=C(C=[N+](C)C)[CH:31]=N1>O>[N+:26]([C:23]1[O:22][C:21]([C:19]2[C:20]([CH:8]=[O:9])=[CH:31][N:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:18]=2)=[CH:25][CH:24]=1)([O-:28])=[O:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 203259884-PyrazolylmethylenedimethylammoniumHCID 858763535-Nitro-2-acetylfuran-phenylhydrazone

Product 1

HCID 203262553-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehydeYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At 10° to 20° C add 77 g of phosphorus oxychloride dropwise to 183 g of dimethylformamide. Stir for 30 minutes at room temperature and, at a temperature not exceeding 40° C, add thereto 55.7 g of 5-nitro-2-acetylfuran-phenylhydrazone. Stir under nitrogen for 1 hour at this temperature and then for 2.5 hours at 50° C. Pour the resulting solution (containing 4-pyrazolylmethylenedimethylammonium salt) onto 2.5 kg of ice and water. Heat for 2 hours at 40° C before vacuum filtering at 20° to 30° C. Wash the residue well with water to obtain a 98% yield of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehyde [m.p. 208° to 209° C (from dimethylformamide/water)].

Workup

  1. customexceeding 40° C
  2. additionadd
  3. stirringStir under nitrogen for 1 hour at this temperature
  4. waitfor 2.5 hours at 50° C
  5. additionPour
  6. temperatureHeat for 2 hours at 40° C before vacuum
  7. filtrationfiltering at 20° to 30° C
  8. washWash the residue well with water

Sources & evidence

ORD record
ord-d4324f1098304197a0615c4fb69e5480
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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