Cyclobutanone → tert-Butyl cyclobutylidenecarbazate

HRID 1478213Notes

Reaction equation

HRID 1478213 reaction equation
[C:1]1(=O)[CH2:4][CH2:3][CH2:2]1.[NH:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[NH2:7]>CCCC(C)C>[C:1]1(=[N:7][NH:6][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14496CyclobutanoneHCID 70091tert-Butyl carbazate

Product 1

HCID 45092398tert-Butyl cyclobutylidenecarbazate

Reagents, catalysts & solvents 1

HCID 78922-MethylpentaneSolvent

Procedure

A mixture of cyclobutanone (16.96 ml, 227 mmol) and tert-butyl hydrazinecarboxylate (30 g, 227 mmol) in isohexane (378 mL), under nitrogen was stirred at reflux for 1 hour. The reaction mixture was cooled to room temperature and stirred for 1 hour. The resulting suspension was filtered, rinsing the solid with iso-hexane (×2). The solid was dried under vacuum at 30° C. to afford the title compound;

Workup

  1. temperatureat reflux for 1 hour
  2. stirringstirred for 1 hour
  3. filtrationThe resulting suspension was filtered
  4. washrinsing the solid with iso-hexane (×2)
  5. customThe solid was dried under vacuum at 30° C.

Sources & evidence

ORD record
ord-6d0cad6218d84abdb6198e828e76072a
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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