Cyclobutanone → tert-Butyl cyclobutylidenecarbazate

HRID 1094539Notes

Reaction equation

HRID 1094539 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]>CCCCCC>[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 cyclobutylidenecarbazateYield 73.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A reaction mixture of cyclobutanone (7.01 g, 100 mmol) and tert-butyl hydrazinecarboxylate (13.22 g, 100 mmol) in hexane (100 mL) was heated under reflux for 2 hours. After cooling down, a precipitate was formed and collected. It was then triturated with isopropanol (5 mL) and hexane (50 mL) to give a white solid as final product tert-butyl 2-cyclobutylidenehydrazinecarboxylate (13.5 g, 73.3 mmol, 73.3% yield). 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 1.50 (s, 9H) 1.96-2.08 (m, 2H) 2.75-2.84 (m, 2H) 2.93-3.05 (m, 2H). MS m/z 207 (M+Na+), Retention time: 1.420 min. (acid).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling down
  4. customa precipitate was formed
  5. customcollected
  6. customIt was then triturated with isopropanol (5 mL) and hexane (50 mL)

Sources & evidence

ORD record
ord-292293fa64af42c099d6de6c8f6ffd55
Source dataset
uspto-grants-2012_03
Patent number
US08133884B2

Reaction notes

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