3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbonyl chloride → 3-(5-Nitro-2-furyl)-1-phenylpyrazole-4-carboxylic acid anhydride

HRID 839241

Reaction equation

HRID 839241 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]([C:26]1[O:30][C:29]([C:31]2[C:35]([C:36]([OH:38])=[O:37])=[CH:34][N:33]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:32]=2)=[CH:28][CH:27]=1)([O-:25])=[O:24]>O1CCOCC1.N1C=CC=CC=1>[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([C:14]([O:38][C:36]([C:35]3[C:31]([C:29]4[O:30][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=4)=[N:32][N:33]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[CH:34]=3)=[O:37])=[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

5

Reactant 2

HCID 203259333-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbonyl chlorideHCID 203259643-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 543639903-(5-Nitro-2-furyl)-1-phenylpyrazole-4-carboxylic acid anhydride

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

Add a solution of 0.64 g of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxylic acid chloride dropwise to a warm solution of 0.60 g of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxylic acid in 10 ml of dioxane and 0.48 ml of pyridine at 40° C. Stir the resulting reaction mixture at from 45° to 50° C for 6 hours. Draw off the formed precipitate and recrystallize it from dimethylformamide to obtain 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxylic acid anhydride [m.p. 262° to 264° C].

Workup

  1. customthe resulting reaction mixture at from 45° to 50° C for 6 hours
  2. customDraw off the formed precipitate and recrystallize it from dimethylformamide

Sources & evidence

ORD record
ord-6cabb35fbf964e4ebfb6a7393a19d1a9
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Linked notes

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