Hydrazine → N'-[(4-cyanophenyl)methylidene]benzenesulfonohydrazide

HRID 464099

Reaction equation

HRID 464099 reaction equation
[C:1]1([S:7]([NH:10][NH2:11])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)#[N:13].NN>C(O)C>[C:1]1([S:7]([NH:10][N:11]=[CH:18][C:17]2[CH:20]=[CH:21][C:14]([C:12]#[N:13])=[CH:15][CH:16]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 65723Benzenesulfonyl hydrazideHCID 660424-Cyanobenzaldehyde

Product 1

HCID 1474568N'-[(4-cyanophenyl)methylidene]benzenesulfonohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Benzenesulfonyl hydrazine (20.5 g, 0.12 mole) was dissolved by warming in 110 ml absolute ethanol. p-Cyanobenzaldehyde (15.6 g, 0.12 mole) was separately dissolved in 50 ml of hot ethanol and added to the hydrazine solution. The resulting slurry was refluxed 0.5 hour, cooled and filtered to yield 28.1 g; m.p. 209°-213°. Recrystallization from CH3CN gave purified title product: 23.7 g; m.p. 210°-213°.

Workup

  1. temperatureThe resulting slurry was refluxed 0.5 hour
  2. temperaturecooled
  3. filtrationfiltered
  4. customto yield 28.1 g
  5. customRecrystallization from CH3CN
  6. customgave
  7. custompurified title product

Sources & evidence

ORD record
ord-2f3ebd3da2dd45cf834f52d28bad5db4
Source dataset
uspto-grants-1985_10
Patent number
US04546113

Linked notes

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