Cyclohexanone Oxime → HCID 86664635, compound

HRID 1183232Notes

Reaction equation

HRID 1183232 reaction equation
[C:1]1(=[N:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[CH:11]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([CH3:22])[CH3:21])[C:15]=1[N:23]=[C:24]=[N:25][C:26]1[C:31]([CH:32]([CH3:34])[CH3:33])=[CH:30][CH:29]=[CH:28][C:27]=1[CH:35]([CH3:37])[CH3:36])([CH3:13])[CH3:12]>C1COCC1>[CH:35]([C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([CH:32]([CH3:34])[CH3:33])[C:26]=1[NH:25][C:24](=[N:23][C:15]1[C:14]([CH:11]([CH3:13])[CH3:12])=[CH:19][CH:18]=[CH:17][C:16]=1[CH:20]([CH3:22])[CH3:21])[O:8][N:7]=[C:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 7517Cyclohexanone OximeHCID 14798Sodium HydroxideHCID 75100Bis(2,6-diisopropylphenyl)carbodiimide

Product 1

HCID 86664635HCID 86664635, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cyclohexanone oxime (1.13 g, 0.01 mol) in dry THF (25 ml) is added finely powdered NaOH (0.04 g) and bis(2,6-diisopropylphenyl)carbodiimide (3.65 g, 0.01 mol). The mixture is then stirred 4 h at room temperature under argon. The turbid mixture is thereafter filtered and evaporated under reduced pressure. The solid residue is crystallized from dichloro-methane-hexane to afford 3.9 g of the title compound as a colorless solid, mp. 150-152° C.

Workup

  1. filtrationThe turbid mixture is thereafter filtered
  2. customevaporated under reduced pressure
  3. customThe solid residue is crystallized from dichloro-methane-hexane

Sources & evidence

ORD record
ord-9849da9accae47f3bc789c007aa4ad4c
Source dataset
uspto-grants-2014_03
Patent number
US08664288B2

Reaction notes

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