Ethanol → 3-(5-Nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehyde-ethoxycarbonylhydrazone

HRID 839216Notes

Reaction equation

HRID 839216 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([CH:14]=O)=[CH:12][N:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:22]([O:26][CH2:27][CH3:28])(=[O:25])[NH:23][NH2:24].C(O)C>C(O)(=O)C.O>[CH2:27]([O:26][C:22]([NH:23][N:24]=[CH:14][C:13]1[C:9]([C:7]2[O:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[N:10][N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=1)=[O:25])[CH3:28]

Participants

6

Reactant 3

HCID 702EthanolHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 203262553-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 544320903-(5-Nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehyde-ethoxycarbonylhydrazoneYield 94%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 962WaterSolvent

Procedure

Stir 48 g of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehyde together with 22 g of ethyl carbazate, 5 drops of glacial acetic acid and 500 ml of ethanol for 3 hours at 60° C. Add 500 ml of water dropwise to the resulting reaction mixture at room temperature. Vacuum filter and wash the obtained precipitate with ethanol/water and with water. Dry the precipitate and then admix it with toluene at 90° C to obtain a 94% yield of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehyde-ethoxycarbonylhydrazone [m.p. 200° to 201° C].

Workup

  1. customdropwise to the resulting reaction mixture at room temperature
  2. filtrationVacuum filter
  3. washwash the obtained precipitate with ethanol/water
  4. customDry the precipitate
  5. customat 90° C

Sources & evidence

ORD record
ord-212a7093e15745a0a96133cf3be64f97
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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