Pyridine → HCID 21547127, compound

HRID 1605654Notes

Reaction equation

HRID 1605654 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([OH:20])[CH3:19])=[CH:10][CH:9]=1.N1C=CC=CC=1.FC(F)(F)C(O)=O.C1(N=C=NC2CCCCC2)CCCCC1.O.O.C(O)(=O)C(O)=O>CCOCC.CO.O.C1C=CC=CC=1.CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:20])[CH3:19])=[CH:10][CH:9]=1

Participants

11

Reactant 5

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 61373Oxalic acid dihydrateHCID 21547081HCID 21547081, compound

Product 1

HCID 21547127HCID 21547127, compound

Reagents, catalysts & solvents 5

HCID 241BenzeneSolventHCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

20.0 Gm (0.0734 mol) of 6-(2'-fluoro-4-biphenylyl)-2-hexanol were dissolved in a mixture consisting of 110 ml of anhydrous dimethyl sulfoxide, 110 ml of absolute benzene, 5.9 ml (0.0732 mol) of pyridine and 2.95 ml (0.0397 mol) of trifluoroacetic acid. 45.5 Gm (0.22 mol) of N,N'-dicyclohexylcarbodiimide were added to the solution, and the mixture was stirred at room temperature for 14 hours. Then, the mixture was diluted with 2 liters of dry ether, a solution of 27.7 gm (0.22 mol) of oxalic acid dihydrate in 180 ml of methanol was added dropwise while stirring, and 2 liters of water were added after the gas evolution, lasting about 30 minutes, was compete. The insoluble N,N' -dicyclohexyl-urea was filtered off, and the aqueous and organic layers were separated. The organic layer was washed twice with aqueous 5% sodium bicarbonate solution and once with water, dried over sodium sulfate and evaporated. The residue was purified by chromatography on silicagel, using benzene as the eluant, and was subsequently recrystallized three times from petroleum ether. Yield: 7.0 gm (35% of theory) of colorless crystals, m.p. 37°-38°C.

Workup

  1. stirringwhile stirring
  2. waitlasting about 30 minutes
  3. filtrationThe insoluble N,N' -dicyclohexyl-urea was filtered off
  4. customthe aqueous and organic layers were separated
  5. washThe organic layer was washed twice with aqueous 5% sodium bicarbonate solution and once with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was purified by chromatography on silicagel
  9. customwas subsequently recrystallized three times from petroleum ether

Sources & evidence

ORD record
ord-e7cb3116c16d4e6aaf8a34fecaa29037
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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