Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1728435Notes

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 chromatogaphy 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-d795d8f87d914874bfd3426394c85519
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05326901

Reaction notes

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