Diethyl Ether → N,N'-Dicyclohexylurea

HRID 1378974Notes

Reaction equation

HRID 1378974 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-8bd830c5a10543fb9fedd701eb542148
Source dataset
uspto-grants-1997_09
Patent number
US05670489

Reaction notes

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