Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 720220

Reaction equation

HRID 720220 reaction equation
C1C(C(O)=[O:8])=CC(C2C3C=CC(O)=CC=3OC3C=2C=CC(C=3)=O)=C(C(O)=O)C=1.ON1C(=O)CCC1=O.[CH:37]1([N:43]=[C:44]=[N:45][CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]2)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>CN(C=O)C>[C:44]([NH:43][CH:37]1[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]1)([NH:45][CH:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1)=[O:8]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 2725051ST51005980

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5- or 6-carboxyfluorescein (0.5 mmol) in dry DMF (5 mL) were added N-hydroxysuccinimide (1.1 equiv.) and 1,3-dicylcohexylcarbodiimide (1.1 equiv.). After about 10 minutes, a white solid (dicyclohexylurea) started forming. The reaction mixture was stirred under nitrogen at room temperature overnight. TLC (thin layer chromatography; 9:1 CH2Cl2—MeOH) indicated complete disappearance of the starting material.

Sources & evidence

ORD record
ord-b54c84f8f5f24bd189c9d319bc479b86
Source dataset
uspto-grants-2006_11
Patent number
US07135300B2

Linked notes

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