Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1901436Notes

Reaction equation

N1(C2C=CN=CC=2)CCCC1.[O:12](C1C=CC(OCCO)=CC=1)C1C=CC=CC=1.FC1(F)CC1CC(O)=O.[CH:38]1([N:44]=[C:45]=[N:46][CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]2)[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>C(Cl)Cl>[CH:47]1([NH:46][C:45]([NH:44][CH:38]2[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]2)=[O:12])[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1

Participants

Conditions

Temperature: 0 °C

Procedure

0.1 g of 4-pyrrolidinopyridine and 2.53 g of 2-(4-phenoxyphenoxy)-ethanol are added to a solution of 1.5 g of 2-(2,2-difluorocyclopropyl)-acetic acid in 20 ml of methylene chloride, and the mixture is cooled to 0° C. At a temperature of from 0° C. to +5° C., a total of 2.5 g of N,N'-dicyclohexylcarbodiimide is added in portions, the ice-cooling is removed and the reaction mixture is allowed to warm to room temperature over a period of 5 hours with stirring. The N,N'-dicyclohexylurea obtained as precipitate is separated off and discarded. The supernatant solution is washed twice with 10 ml of water each time, dried over magnesium sulfate and concentrated by evaporation. The residue is purified by column chromatography on silica gel (eluant: hexane/ethyl acetate, 85:15), yielding pure 2-(2,2-difluorocyclopropyl)-acetic acid 2-(4-phenoxyphenoxy)-ethyl ester in the form of a yellowish oil having a refractive index of nD22 : 1.5309.

Workup

customis removed
temperatureto warm to room temperature over a period of 5 hours

Sources & evidence

ORD record: ord-23afabffc778405d8af310d2ead6330e
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05578595

Reaction notes

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