2-Chlorocyclohexanone → HCID 12696967, compound

HRID 1951537Notes

Reaction equation

HRID 1951537 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[C:9]([NH2:12])(=[S:11])[CH3:10]>C(O)C>[CH3:10][C:9]1[S:11][C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=2[N:12]=1

Participants

4

Reactant 2

HCID 132032-ChlorocyclohexanoneHCID 2723949Thioacetamide

Product 1

HCID 12696967HCID 12696967, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.00 g (37.7 mmol) of 2-chlorocyclohexanone and 2.83 g (37.7 mmol) of thioacetamide are heated in 25 ml of ethanol at the reflux temperature overnight. After cooling, the volatile components are removed in a rotary evaporator, and the remaining residue is taken up in 2 N sodium carbonate solution. It is extracted three times with dichloromethane, and the combined organic phases are dried with magnesium sulfate. The solvent is removed in a rotary evaporator, and the residue is then purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 7:3). 3.35 g (58% of theory) of the title compound are obtained.

Workup

  1. temperatureAfter cooling
  2. customthe volatile components are removed in a rotary evaporator
  3. extractionIt is extracted three times with dichloromethane
  4. dry with materialthe combined organic phases are dried with magnesium sulfate
  5. customThe solvent is removed in a rotary evaporator
  6. customthe residue is then purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-998992d07ed34be5baa5981c10b04b23
Source dataset
uspto-grants-2013_03
Patent number
US08404723B2

Reaction notes

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