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

HRID 437522Notes

Reaction equation

HRID 437522 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

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 3310889(4-Nitrophenyl)hydrazine

Product 1

HCID 31065344-Chlorobenzoic N2-(4-nitrophenyl)hydrazide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

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

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with acetonitrile
  3. customThe product was recrystallized from acetonitrile
  4. customto give a pale yellow solid

Sources & evidence

ORD record
ord-4b746da966c34400b23ef63dff0892d1
Source dataset
uspto-grants-1977_06
Patent number
US04031127

Reaction notes

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