Dicyclohexylcarbodiimide → HCID 18205828, compound

HRID 1871833Notes

Reaction equation

C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([OH:23])(=[O:22])/[CH:17]=[CH:18]/[CH:19]=[CH:20]/[CH3:21].[C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)#[N:25]>ClCCl.CN(C)C1C=CN=CC=1>[C:16]([O:23][C:35]1[CH:34]=[CH:33][C:32]([C:29]2[CH:28]=[CH:27][C:26]([C:24]#[N:25])=[CH:31][CH:30]=2)=[CH:37][CH:36]=1)(=[O:22])/[CH:17]=[CH:18]/[CH:19]=[CH:20]/[CH3:21]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of N,N'-dicyclohexylcarbodiimide (0.87 g, 0.0042 mol) in dichloromethane (10 CM3) was added to a solution of (E,E)-hexa-2,4-dienoic acid (0.47 g, 0.0042 mol), 4-cyano-4'-hydroxybiphenyl (0.67 g, 0.0035 mol), 4-(dimethylamino)pyridine (0.05 g) in dichoromethane (25 cm3), cooled in an ice bath (0° C.) under an atmosphere of nitrogen. The reaction mixture was stirred overnight, filtered to remove precipitated material and the filtrate was evaporated down under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane as eluent, followed by recrystallisation from a 1:1 ethanol/ethyl acetate mixture to yield 0.76 g (76%). K 160° C., N-I 227° C.

Workup

filtrationfiltered
customto remove
customprecipitated material
customthe filtrate was evaporated down under reduced pressure
customThe crude product was purified by column chromatography on silica gel
customfollowed by recrystallisation from a 1:1 ethanol/ethyl acetate mixture
customto yield 0.76 g (76%)
customK 160° C., N-I 227° C.

Sources & evidence

ORD record: ord-b89ca835262143cc9301f667c54791bd
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06106908

Reaction notes

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