Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 65183Notes

Reaction equation

HRID 65183 reaction equation
C(SCC(O)=O)(=[O:3])C.ON1C(=O)CCC1=O.[CH:17]1([N:23]=[C:24]=[N:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>O1CCOCC1>[CH:26]1([NH:25][C:24]([NH:23][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)=[O:3])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 14485Acetic acid, 2-(acetylthio)-HCID 80170N-Hydroxysuccinimide

Product 1

HCID 4277N,N'-DicyclohexylureaYield 66%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

S-Acetyl-2-mercaptoacetic acid (75 mmoles) and N-hydroxysuccinimide (75 mmoles), were dissolved in 150 ml dioxane and reacted with cooling in ice with N,N'-dicyclohexylcarbodiimide (75 mmoles) and the mixture was kept at 4° C. for 16 h. The N,N'-dicyclohexylurea formed was removed by filtration and the solvent evaporated in vacuo. The residue was twice recrystallized from 2-propanol.

Workup

  1. customreacted

Sources & evidence

ORD record
ord-18d7f9d78b7d45a9ae44c5daeaa0ef03
Source dataset
uspto-grants-1986_09
Patent number
US04613587

Reaction notes

Loading…