Dichloromethane → N,N'-Dicyclohexylurea

HRID 1683701Notes

Reaction equation

ClCCl.[CH:4]1([N:10]=[C:11]=[N:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.CCCCC(O)=[O:24]>>[CH:13]1([NH:12][C:11]([NH:10][CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)=[O:24])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 7991Pentanoic Acid

HCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 4277N,N'-Dicyclohexylurea

Conditions

Temperature: 25 °C

Procedure

To a solution of a 2.5g (7.68 mmol) portion of the product of Example 26 in 40 ml of anhydrous dichloromethane 4.75 g (23 mmol) of dicyclohexylcarbodiimide and 2.88 g (23 mmol) of n-valeric acid were added and the reaction mixture was maintained at 25° C. under intermittent stirring for 24 hours. Then the N,N'-dicyclohexylurea formed as by-product was filtered, the filtrate was evaporated under reduced pressure, the residue was mixed with 2×40 ml of distilled water, decanted and the wet product was left to solidify under 50 ml of 50% ethanol. The solid compound was filtered, washed with 2×10 ml of 50% ethanol and dried at 80° C. The raw product obtained was recrystallized from 24 ml of ethanol and the crystals were dried at 100° C. to yield 2.20 g (70%) of the aimed product as a yellow powder, m.p.: 145°-147° C.

Sources & evidence

ORD record: ord-8c6f65bce8824d39972506487fe27e0a
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639751

Reaction notes

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