Diethyl Ether → N,N'-Dicyclohexylurea

HRID 128915Notes

Reaction equation

HRID 128915 reaction equation
CC(C)C[OH:4].CN(C1C=CC=CN=1)C.[CH:15]1([N:21]=[C:22]=[N:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.CCOCC>O1CCCC1.CCCCCC>[C:22]([NH:21][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)([NH:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:4]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6560IsobutanolHCID 10868DicyclohexylcarbodiimideHCID 218852-Dimethylaminopyridine

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Compound 47 (0.45 g., 0.83 mmole) is dissolved in tetrahydrofuran (5 ml.) and 2-methylpropan-1-ol (0.07 g., 0.99 mmole), dimethylaminopyridine (50 mg.), and dicyclohexylcarbodiimide (0.205 g., 0.99 mmole) are added. The mixture is stirred for three hours. Ether (15 ml.) and hexane (5 ml.) are added, the dicylohexylurea formed is filtered off and the solvent is evaporated. The residual oil is purified by chromatography on silica using 2% methanol in ethyl acetate as eluant, to give Compound 48.

Sources & evidence

ORD record
ord-f96578ee4ac94ac09cd54f004fbdf205
Source dataset
uspto-grants-1995_11
Patent number
US05466677

Reaction notes

Loading…