Cyclohexanone Oxime → HCID 86664637, compound

HRID 1183234Notes

Reaction equation

HRID 1183234 reaction equation
[C:1]1(=[N:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[CH:11]1([N:17]=[C:18]=[N:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C1COCC1.ClCCl>[CH:20]1([NH:19][C:18](=[N:17][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[O:8][N:7]=[C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

6

Reactant 3

HCID 7517Cyclohexanone OximeHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium Hydroxide

Product 1

HCID 86664637HCID 86664637, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cyclohexanone oxime (5.65 g, 0.05 mol) in dry THF (30 ml) is added finely powdered NaOH (0.2 g) and dicyclohexylcarbodiimide (11.34 g, 0.055 mol). The mixture is then stirred 5 h at room temperature under argon. The turbid mixture is thereafter diluted with dichloromethane (25 ml), filtered and evaporated under reduced pressure. The residue is stirred 10 minutes with acetonitrile (30 ml), the acetonitrile phase is then discarded, the oily residue is dissolved in dichloromethane (30 ml), filtered and evaporated to afford 14.27 g of the title compound as a slightly yellow liquid.

Workup

  1. filtrationfiltered
  2. customevaporated under reduced pressure
  3. stirringThe residue is stirred 10 minutes with acetonitrile (30 ml)
  4. dissolutionthe oily residue is dissolved in dichloromethane (30 ml)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-5b5a84a8cd6447cd9324750f94de213a
Source dataset
uspto-grants-2014_03
Patent number
US08664288B2

Reaction notes

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