Acetic Acid → HCID 53808139, compound

HRID 839215Notes

Reaction equation

HRID 839215 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[NH:2][NH2:3].[CH3:8][N:9]1[CH:13]=[C:12]([CH:14]=O)[C:11]([C:16]2[O:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=2)=[N:10]1.C(O)(=O)C.O>C(O)C>[CH2:6]([O:5][C:1]([NH:2][N:3]=[CH:14][C:12]1[C:11]([C:16]2[O:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=2)=[N:10][N:9]([CH3:8])[CH:13]=1)=[O:4])[CH3:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962Water2×HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 203259351-Methyl-3-(5-nitrofuran-2-yl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 53808139HCID 53808139, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Add a solution of 19.5 g of ethyl carbazate in 250 ml of ethanol dropwise to 35 g of 1-methyl-3-(5-nitro-2-furyl)pyrazole-4-carboxaldehyde and 1 ml of glacial acetic acid in 400 ml of ethanol. Stir the resulting reaction mixture for 80 minutes at from 35° to 40° C, and add 650 ml of water dropwise to the thus-obtained suspension at room temperature. Cool in an ice bath and separate the produced precipitate by vacuum filtration. Wash the residue with ethanol/water (1:1) and with water to obtain a 97% yield of 1-methyl-3-(5-nitro-2-furyl)pyrazole-4-carboxaldehyde-ethoxycarbonylhydrazone [m.p. 217.5° to 219° C (with decomposition)].

Workup

  1. customthe resulting reaction mixture for 80 minutes at from 35° to 40° C
  2. temperatureCool in an ice bath
  3. customseparate the produced precipitate
  4. filtrationby vacuum filtration
  5. washWash the residue with ethanol/water (1:1)

Sources & evidence

ORD record
ord-cc6d181966e947338eff96b90ae98aa1
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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