Dicyclohexylcarbodiimide → HCID 86664636, compound

HRID 1183233Notes

Reaction equation

HRID 1183233 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-48e45b6dd1264a86843c18f832fa567e
Source dataset
uspto-grants-2014_03
Patent number
US08664288B2

Reaction notes

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