Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 623251Notes

Reaction equation

HRID 623251 reaction equation
[OH:1]N1C(=O)CCC1=O.[CH:9]1([N:15]=[C:16]=[N:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>C(OCC)(=O)C>[CH:18]1([NH:17][C:16]([NH:15][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)=[O:1])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 120 mg (0.37 mmol) 2 in 10 ml of ethyl acetate was added 43 mg (0.37 mmol) N-hydroxysuccinimide followed by addition of 85 mg (0.41 mmol) N,N'-dicyclohexylcarbodiimide. The mixture was stirred at room temperature for 24 hours. The N,N'-dicyclohexylurea which formed was removed by filtration and the filtrate was evaporated to dryness under reduced pressure to give an orange-red solid. It was purified by chromatography on silica gel with chloroform as eluant to give 118 mg (77%) of orange-red needles of 3. Succinimidyl esters 6 and 9 were prepared by similar procedures.

Sources & evidence

ORD record
ord-2c3ab06893944b71b2e394174ad5472e
Source dataset
uspto-grants-1988_09
Patent number
US04774339

Reaction notes

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