Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 48896Notes

Reaction equation

HRID 48896 reaction equation
[OH:1]N1C(=O)CCC1=O.[CH2:9]1[CH2:14][CH2:13][CH:12]([N:15]=[C:16]=[N:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:11][CH2:10]1>C(OCC)(=O)C>[CH:18]1([NH:17][C:16]([NH:15][CH:12]2[CH2:11][CH2:10][CH2:9][CH2:14][CH2:13]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 AcetateSolvent2×

Procedure

The copolymer was fed into a round-bottomed flask and dissolved in a half amount (25 to 30 mL) of ethyl acetate. Next, N-hydroxysuccinimide and DCC were added thereto followed by dissolution in the residual ethylacetate. The obtained mixture was immersed in ice-water at 4° C. and stirred with a stirrer for 2 hours. Subsequently, it was introduced into a thermostat at 25° C. and stirred therein overnight. The solution was filtered and thus dicyclohexyl urea formed as a by product was removed therefrom. After concentrating under reduced pressure, the residue was purified with diethyl ether. The product thus obtained was taken up by filtration and dried under reduced pressure. The succinylated copolymer thus obtained was stored in a freezer.

Workup

  1. customThe copolymer was fed into a round-bottomed flask
  2. additionSubsequently, it was introduced into a thermostat at 25° C.
  3. stirringstirred
  4. customovernight
  5. filtrationThe solution was filtered

Sources & evidence

ORD record
ord-04f9ce3b4a994751845b4f99bd59f232
Source dataset
uspto-grants-2004_03
Patent number
US06706187B1

Reaction notes

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