Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1669628Notes

Reaction equation

HRID 1669628 reaction equation
[OH:1]C1C=C(O)C=CC=1CC(O)=O.[CH2:13]1[CH2:18][CH2:17][CH:16]([N:19]=[C:20]=[N:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:15][CH2:14]1>C(OCC)(=O)C.CCCCCC>[CH:22]1([NH:21][C:20](=[O:1])[NH:19][CH:16]2[CH2:15][CH2:14][CH2:13][CH2:18][CH2:17]2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 69199Benzeneacetic acid, 2,4-dihydroxy-

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.5 g of 2,4-dihydroxyphenylacetic acid (1.8 mole) was dissolved in 20 mL of 50:50 v/v ethyl acetate and hexane. Then 1.5 mL of DCC (˜1.4 mmole) was added and the reaction continued for 1 hr at room temperature under argon that was bubbled into the solution. A white precipitate of dicyclohexyl urea formed during the reaction. After 3 hr. the urea precipitate was removed and 1.8 mL (5.6 mmol) of oleylamine (C18-content 80-90%; Fisher), was initially dissolved in 10 mL of hexane in the presence of 4-dimethylaminopyridine (0.5 g) and added to the reaction product of the 2,4-dihydroxyphenylacetic acid and DCC. The reaction continued at room temperature for 1 hr and then stored at −20° C. for one week.

Workup

  1. customthat was bubbled into the solution

Sources & evidence

ORD record
ord-f12b4bdda5ce400199bed34f6f77ba50
Source dataset
uspto-grants-2011_08
Patent number
US07989499B2

Reaction notes

Loading…