Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 329910Notes

Reaction equation

HRID 329910 reaction equation
[CH:1]1([N:7]=[C:8]=[N:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(=O)N(NCCCCCC(O)=[O:28])C(=O)C=C1>CN(C=O)C>[CH:10]1([NH:9][C:8]([NH:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[O:28])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 19361018N-maleimido-6-aminocaproic acid

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

One equivalent (2.24 g, 0.01 mole) of HNSA was mixed together - with one equivalent (2.06 g, 0.01 mole) of dicyclohexylcarbodiimide and one equivalent (2.10 g, 0.01 mole) of N-maleimido-6-aminocaproic acid in 25 ml of DMF at room temperature overnight. A white precipitate of dicyclohexyl urea was formed. The precipitate was filtered and 300 ml diethyl ether was added to the mother liquor. After about 10 minutes to four hours a gummy solid that precipitated from the mother liquor was formed. This solid was found to contain 58% of active HNSA ester and 42% of free HNSA by the analysis described above. The product was positively identified as mal-sac-HNSA ester by its reactivity with amines. The yield of the pure ester was estimated to be approximately 30% of theoretical; the purified material consisted of 99% ester.

Sources & evidence

ORD record
ord-31b79e92a0c14049a8f44899af34fda1
Source dataset
uspto-grants-1990_01
Patent number
US04894226

Reaction notes

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