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

HRID 839230Notes

Reaction equation

HRID 839230 reaction equation
Cl([O-])(=O)(=O)=O.[N+:6]([C:9]1[O:13][C:12]([C:14]2[C:18]([CH:19]=[N+](C)C)=[CH:17][N:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:15]=2)=[CH:11][CH:10]=1)([O-:8])=[O:7].C([O-])(=O)C.[Na+].[C:34]([O:38][CH2:39][CH3:40])(=[O:37])[NH:35][NH2:36].CN(C)C=O>O>[CH2:39]([O:38][C:34]([NH:35][N:36]=[CH:19][C:18]1[C:14]([C:12]2[O:13][C:9]([N+:6]([O-:8])=[O:7])=[CH:10][CH:11]=2)=[N:15][N:16]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:17]=1)=[O:37])[CH3:40]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 517045Sodium AcetateHCID 20326261[3-(5-Nitro-2-furyl)-1-phenylpyrazol-4-ylmethylene]dimethylammonium perchlorate

Product 1

HCID 544320903-(5-Nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehyde-ethoxycarbonylhydrazoneYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 2.0 g of [3-(5-nitro-2-furyl)-1-phenylpyrazol-4-ylmethylene]dimethylammonium perchlorate, 0.4 g. of anhydrous sodium acetate and 0.63 g of ethyl carbazate to 10.5 ml of dimethylformamide. Stir the resulting admixture for 30 minutes before adding 30 ml of water dropwise thereto to obtain a 95% yield of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehyde-ethoxycarbonylhydrazone [m.p. 200° to 201° C].

Sources & evidence

ORD record
ord-a47b076446b545788df58a0a1bc54ef4
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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