Sodium Azide → 3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbonyl azide

HRID 839240

Reaction equation

HRID 839240 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([C:14](Cl)=[O:15])=[CH:12][N:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N-:23]=[N+:24]=[N-:25].[Na+]>CC(C)=O.O1CCOCC1.O>[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([C:14]([N:23]=[N+:24]=[N-:25])=[O:15])=[CH:12][N:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 203259333-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbonyl chloride

Product 1

HCID 545094763-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbonyl azideYield 98%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

At from 23° to 30° C add a warm solution of 7.5 g of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxylic acid chloride in 200 ml of acetone and 250 ml of dioxane dropwise to a solution of 1.84 g of sodium azide in 24 ml of water. Stir the resulting reaction mixture for a further 15 minutes and then dilute it with 600 ml of water cooling with ice to obtain a 98% yield of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxylic acid azide [m.p. 134° C (with decomposition)].

Workup

  1. customthe resulting reaction mixture for a further 15 minutes

Sources & evidence

ORD record
ord-89506c956df84db3ac573c6f9297ad3b
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Linked notes

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