Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1088203Notes

Reaction equation

HRID 1088203 reaction equation
[Na+].[OH:2]C1C=CC(S([O-])(=O)=O)=CC=1[N+]([O-])=O.[CH:16]1([N:22]=[C:23]=[N:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C1(=O)N(NCCCCCC(O)=O)C(=O)C=C1>CN(C)C=O>[C:23]([NH:22][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)([NH:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 12598197Sodium 4-hydroxy-3-nitrobenzenesulfonateHCID 19361018N-maleimido-6-aminocaproic acid

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

One molar equivalent (2.24 g) of 4-hydroxy-3-nitrobenzene sulfonic acid sodium salt (HNSA) was mixed together with one molar equivalent (2.06 g) of dicyclohexylcarbodiimide and one molar equivalent (2.10 g) of N-maleimido-6-aminocaproic acid in 25 mL of dimethylformamide (DMF) at room temperature overnight. A white precipitate of dicyclohexylurea was formed. The precipitate was filtered and 300 mL diethyl ether was added to the mother liquor. After about 10 minutes to 4 hours a gummy solid precipitated from the mother liquor. This solid was found to contain 58% of active HNSA ester and 42% of free HNSA.

Sources & evidence

ORD record
ord-67e9610f02c747bfbb22771156e893cf
Source dataset
uspto-grants-1990_10
Patent number
US04962029

Reaction notes

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