1,1-Dimethylhydrazine → Cyclohexanone dimethylhydrazone

HRID 1893337Notes

Reaction equation

HRID 1893337 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:8][N:9]([CH3:11])[NH2:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[C:1]1(=[N:10][N:9]([CH3:11])[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 59761,1-DimethylhydrazineHCID 7967CyclohexanoneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 277542Cyclohexanone dimethylhydrazoneYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To solution of cyclohexanone (2.00 g, 20.4 mmol) and N,N-dimethylhydrazine (1.50 ml, 20.4 mmol) in ethanol (20 ml) was added a catalytic amount of toluene-4-sulfonic acid monohydrate. The reaction mixture was stirred at 70° C. for 72 h. The solvent was evaporated, and the residue was purified by Kugelrohr distillation (60-80° C., 5 mbar) to give the title compound (2.50 g, 87%) as colorless oil. MS m/e: 141 ([M+H]+)

Workup

  1. customThe solvent was evaporated
  2. distillationthe residue was purified by Kugelrohr distillation (60-80° C., 5 mbar)

Sources & evidence

ORD record
ord-e29bbbc36db244f282b1905f58f5077d
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

Loading…