Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1493459Notes

Reaction equation

HRID 1493459 reaction equation
C(N(CC(O)=O)CCN(CC(O)=O)CC(O)=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=[O:9].ON1C(=O)CCC1=O.[CH:43]1([N:49]=[C:50]=[N:51][CH:52]2[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]2)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1>CS(C)=O>[CH:52]1([NH:51][C:50](=[O:9])[NH:49][CH:43]2[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]2)[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 700883,6,9,12-Tetrakis(carboxymethyl)-3,6,9,12-tetraazatetradecanedioic acidHCID 80170N-Hydroxysuccinimide

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution consisting of 0.7 g (1.3 mmol) N,N'-(2-aminoethyl) trans-1,2-diaminocyclohexane-N,N',N",N'",N'"hexaacetic acid in 50 ml dimethylsulfoxide was added 0.9 g (7.8 mmol) N-hydroxysuccinimide and 0.8 g (3.9 mmol) dicyclohexylcarbodiimide. This was stirred at room temperature for 48 hr., during which the white fluffy solid of dicyclohexyl urea formed. This solid was removed by filtration and the filtrate was concentrated to a thick oil under reduced pressure. A solid precipitated from the oil upon the addition of acetonitrile. This solid was collected, washed with cold acetonitrile and dried under vacuum to give 0.54 g of a light brown solid. NMR showed an average of 2 NHS esters so the yield is 56%. No further purification of the solid was attempted; mp 125°-140° C.

Sources & evidence

ORD record
ord-2afdaad5e4ef4ac9be98e60a4c91f1a9
Source dataset
uspto-grants-1991_06
Patent number
US05021571

Reaction notes

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