Dicyclohexylcarbodiimide → HCID 131717912, compound

HRID 248776Notes

Reaction equation

HRID 248776 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:16][CH:15]=3)=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[F:27][C:28]([CH3:36])([CH2:32][CH2:33][CH2:34][CH3:35])[C:29]([OH:31])=[O:30].[CH:37]1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[F:27][C:28]([CH3:36])([CH2:32][CH2:33][CH2:34][CH2:35][CH3:37])[C:29]([O:31][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:16][CH:15]=3)=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1)=[O:30]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1370672674106-60-8HCID 131717913HCID 131717913, compound

Product 1

HCID 131717912HCID 131717912, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

240 mg (0.7 mmol) of 4-hydroxy-4"-hexyloxyterphenyl, 20 mg (0.7 mmol) of (-)-2-fluoro-2-methylhexanoic acid, 150 mg (0.7 mmol) of N,N'-dicyclohexylcarbodiimide and 10 mg (0.07 mmol) of 4-dimethylaminopyridine were dissolved in 100 ml of dried dichloromethane, which were stirred under reflux for 7 hours. After the completion of the reaction, the precipitate was removed by filtration and then the filtrate was washed with 1 normal hydrochloric acid and further with water, after which the organic phase was dried on anhydrous magnesium sulfate. After the removal of magnesium sulfate by filtration, the filtrate was purified through a column chromatography of silica gel with toluene as a developing solvent and recrystallized from 60 ml of ethanol to obtain 80 mg (yield: 24%) of a white crystal. The thus obtained compound has the aforementioned physical and chemical properties.

Workup

  1. temperatureunder reflux for 7 hours
  2. customAfter the completion of the reaction
  3. customthe precipitate was removed by filtration
  4. washthe filtrate was washed with 1 normal hydrochloric acid and further with water
  5. dry with materialafter which the organic phase was dried on anhydrous magnesium sulfate
  6. customAfter the removal of magnesium sulfate
  7. filtrationby filtration
  8. customthe filtrate was purified through a column chromatography of silica gel with toluene as a developing solvent
  9. customrecrystallized from 60 ml of ethanol

Sources & evidence

ORD record
ord-5b4620846ba74754a532aedaeece6754
Source dataset
uspto-grants-1993_05
Patent number
US05211879

Reaction notes

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