tert-Butyl carbazate → Tert-butyl 2-(3-cyanobenzylidene)-1-hydrazinecarboxylate

HRID 1181188Notes

Reaction equation

HRID 1181188 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].[C:11]([O:15][C:16](=[O:19])[NH:17][NH2:18])([CH3:14])([CH3:13])[CH3:12]>CCO>[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[N:18][NH:17][C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:19])#[N:2]

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 90670m-Formylbenzonitrile

Product 1

HCID 69314844Tert-butyl 2-(3-cyanobenzylidene)-1-hydrazinecarboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-Cyanobenzaldehyde (40.0 mmol) suspended in EtOH (100 mL) was added to a stirred solution of tert-butylcarbazate (40.0 mmol) in EtOH. The mixture was heated at reflux temperature and after 4 h the EtOH was partially evaporated in vacuo. Water (100 mL) was added and the precipitated product was collected by filtration and washed with diethylether to give tert-butyl 2-(3-cyanobenzylidene)-1-hydrazinecarboxylate as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature
  3. customafter 4 h the EtOH was partially evaporated in vacuo
  4. additionWater (100 mL) was added
  5. filtrationthe precipitated product was collected by filtration
  6. washwashed with diethylether

Sources & evidence

ORD record
ord-d57f2d9fe43d421ca4219b3e149b9522
Source dataset
uspto-grants-2007_10
Patent number
US07285547B2

Reaction notes

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