2-Butanone oxime → 1,3-Dicyclohexyl-O-(N-2-butylideneamino)-isourea

HRID 1183230Notes

Reaction equation

HRID 1183230 reaction equation
[CH3:1][C:2](=[N:5][OH:6])[CH2:3][CH3:4].[CH:7]1([N:13]=[C:14]=[N:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>C1COCC1.[OH-].[Na+]>[CH:16]1([NH:15][C:14](=[N:13][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[O:6][N:5]=[C:2]([CH2:3][CH3:4])[CH3:1])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

5

Reactant 2

HCID 72922-Butanone oximeHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 866646331,3-Dicyclohexyl-O-(N-2-butylideneamino)-isoureaYield 76.6%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methylethylketone oxime (4.6 g, 0.053 mol) in dry THF (30 ml) is added finely powdered NaOH (0.15 g) and dicyclohexylcarbodiimide (10.3 g, 0.05 mol). The mixture is then stirred 5 h at room temperature under argon. The turbid mixture is thereafter 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 11.24 g of the title compound as a slightly yellow liquid.

Workup

  1. filtrationThe turbid mixture is thereafter filtered
  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-f82b7ea3cd4e4be88badaef144abbde3
Source dataset
uspto-grants-2014_03
Patent number
US08664288B2

Reaction notes

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