Dicyclohexylcarbodiimide → HCID 86664638, compound

HRID 1183236Notes

Reaction equation

HRID 1183236 reaction equation
[C:1]1(=[N:13][OH:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:15]1([N:21]=[C:22]=[N:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>CCCCCC>[CH:24]1([NH:23][C:22](=[N:21][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[O:14][N:13]=[C:1]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 136762Cyclododecanone, oxime

Product 1

HCID 86664638HCID 86664638, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of cyclododecanone oxime (19.73 g, 100 mmol), dicyclohexylcarbodiimide (20.63 g, 100 mmol) and potassium-t-butylate (0.12 g) in hexane (75 ml) is stirred 23 h at 50° C. under argon. The mixture is then allowed to crystallize overnight at −18° C. The solid is filtered off and recrystallized from dichloromethane-hexane to afford 17.4 g of the title compound as white solid, mp. 108-111° C.

Workup

  1. customto crystallize overnight at −18° C
  2. filtrationThe solid is filtered off
  3. customrecrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-33f7b97e14b443d1b99bfc333906270f
Source dataset
uspto-grants-2014_03
Patent number
US08664288B2

Reaction notes

Loading…