Dimethylformamide → 3-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbonyl chloride

HRID 839239

Reaction equation

HRID 839239 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([C:14](N)=[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].S(Cl)([Cl:25])=O.CN(C)C=O>C(Cl)(Cl)(Cl)Cl>[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([C:14]([Cl: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

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 203261233-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carboxamide

Product 1

HCID 203259333-(5-Nitrofuran-2-yl)-1-phenyl-1H-pyrazole-4-carbonyl chlorideYield 89%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Heat 40 g of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxamide together with 290 ml of thionyl chloride and 1 ml of dimethylformamide for 16 hours at boiling point. Cool the resulting solution, draw off the formed precipitate and wash it with thionyl chloride and with carbon tetrachloride to obtain an 89% yield of 3-(5-nitro-2-furyl)-1-phenylpyrazole-4-carboxylic acid chloride [m.p. 208° to 210° C (from dioxane)].

Workup

  1. temperatureCool the resulting solution
  2. washwash it with thionyl chloride

Sources & evidence

ORD record
ord-d080d09299164235ae3fa50ae9ad0846
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Linked notes

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