Dimethylformamide → N-{[3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl]methylidene}hydroxylamine

HRID 839231Notes

Reaction equation

HRID 839231 reaction equation
Cl([O-])(=O)(=O)=O.[N+:6]([C:9]1[O:13][C:12]([C:14]2[C:18]([CH:19]=[N+:20](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:31])C.[Na+].Cl.NO.CN(C)C=O>O>[N+:6]([C:9]1[O:13][C:12]([C:14]2[C:18]([CH:19]=[N:20][OH:31])=[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]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 20326261[3-(5-Nitro-2-furyl)-1-phenylpyrazol-4-ylmethylene]dimethylammonium perchlorate

Product 1

HCID 54343732N-{[3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazol-4-yl]methylidene}hydroxylamineYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 2.0 g of [3-(5-nitro-2-furyl)-1-phenylpyrazol-4-ylmethylene]dimethylammonium perchlorate, 0.42 g of anhydrous sodium acetate and 0.36 g of hydroxylamine hydrochloride to 11 ml of dimethylformamide. Stir the resulting admixture for 2 hours at room temperature before adding 30 ml of water dropwise thereto to precipitate the title compound for a 95% yield of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxaldehydeoxime [m.p. 199° to 201° C (with decomposition)].

Sources & evidence

ORD record
ord-bb0f5206e89c486197f6322da9fd6ad6
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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