Diethyl Ether → N,N'-Dicyclohexylurea

HRID 1720872Notes

Reaction equation

HRID 1720872 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 63 (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 (1 5 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 64.

Sources & evidence

ORD record
ord-40d26390700f4d1298933a1f407daef7
Source dataset
uspto-grants-1996_04
Patent number
US05508270

Reaction notes

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