4-Chlorobenzoyl chloride → 4-Chlorobenzoic N2-(4-nitrophenyl)hydrazide

HRID 437300

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1>C(#N)C>[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:11][NH:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[O:18])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Nitrophenylhydrazine (32.0 g, 0.21 mole) was slurried in acetonitrile (500 ml) and the mixture was cooled to 0° C. A solution of 4-chlorobenzoyl chloride (17.5 g, 0.10 mole) in acetonitrile (25 ml) was added dropwise to the cooled slurry. The reaction mixture was allowed to stand overnight. The mixture was filtered and the solid was washed with acetonitrile, then thoroughly with water. The product was recrystallized from acetonitrile and decolorized with charcoal to give a pale yellow solid. Yield 24.8 g (85%) m.p. 245.5°-248.5° C.

Workup

filtrationThe mixture was filtered
washthe solid was washed with acetonitrile
customThe product was recrystallized from acetonitrile
customto give a pale yellow solid

Sources & evidence

ORD record: ord-dcc1940639ff4d9292a6efc96f2e2c56
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04030925

Linked notes

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