Dicyclohexylcarbodiimide → 4-[3,5-Bis(decyloxy)phenyl]2,6-morpholinedione

HRID 1757793Notes

Reaction equation

HRID 1757793 reaction equation
[C:1]([CH2:4][N:5]([C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:13]=[C:12]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8])(O)=[O:2].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH2:17]([O:16][C:14]1[CH:15]=[C:10]([N:5]2[CH2:4][C:1](=[O:2])[O:8][C:7](=[O:9])[CH2:6]2)[CH:11]=[C:12]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:13]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 192621N-(carboxymethyl)-N-(3,5-bis(decyloxy)-phenyl)glycine

Product 1

HCID 193890794-[3,5-Bis(decyloxy)phenyl]2,6-morpholinedioneYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2.0 g (3.83 mmol) of N-(carboxymethyl)-N-[3,5-bis(decyloxy)phenyl]glycine in 100 ml of methylene chloride stirred at room temperature was added 0.9 g (4.37 mmol)of dicyclohexylcarbodiimide The reaction mixture was stirred at room temperature for 17 hours. After cooling in an ice bath, the precipitate was removed by filtration and the filtrate was concentrated at reduced pressure to a solid which was recrystallized from hexane to give 1.7 g (88% yield, mp 62°-62°) of 4-[3,5-bis(decyloxy)phenyl]2,6-morpholinedione.

Workup

  1. temperatureAfter cooling in an ice bath
  2. customthe precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated at reduced pressure to a solid which
  4. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-bb2c247904964139984aeeb866c75321
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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