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

HRID 569502

Reaction equation

HRID 569502 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-774cb67f10974ed1b56b581437b1501f
Source dataset
uspto-grants-1988_03
Patent number
US04732907

Linked notes

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