Dicyclohexylcarbodiimide → HCID 86664636, compound

HRID 2275472Notes

Reaction equation

HRID 2275472 reaction equation
[C:1](=[N:14][OH:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH:18]1([N:24]=[C:25]=[N:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C1COCC1>[CH:27]1([NH:26][C:25](=[N:24][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[O:15][N:14]=[C:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11324Benzophenone oximeHCID 14798Sodium Hydroxide

Product 1

HCID 86664636HCID 86664636, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzophenone oxime (3.94 g, 0.02 mol) in dry THF (40 ml) is added finely powdered NaOH (0.08 g) and dicyclohexylcarbodiimide (4.25 g, 0.0206 mol). The mixture is then stirred 22 h at room temperature under argon. The turbid mixture is thereafter filtered and evaporated under reduced pressure. The residue is crystallized from acetonitrile and again from acetonitrile-dichloromethane-hexane to afford 2.93 g of the title compound as a colorless solid, mp. 104-107° C.

Workup

  1. filtrationThe turbid mixture is thereafter filtered
  2. customevaporated under reduced pressure
  3. customThe residue is crystallized from acetonitrile and again from acetonitrile-dichloromethane-hexane

Sources & evidence

ORD record
ord-dde11d8b70af4f5aab5eea5a6c54b7ed
Source dataset
uspto-grants-2015_09
Patent number
US09127098B2

Reaction notes

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