Pyridine → HCID 178427746, compound

HRID 1590017Notes

Reaction equation

HRID 1590017 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.N1C=CC=CC=1.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>O>[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([O:1][CH2:2][C@H:3]2[CH2:8][CH2:7][C@H:6]([C:9]3[CH:10]=[CH:11][C:12]([C:13]#[N:14])=[CH:15][CH:16]=3)[CH2:5][CH2:4]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 73974-Toluenesulfonyl chlorideHCID 178509804HCID 178509804, compound

Product 1

HCID 178427746HCID 178427746, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Into a 1 l capacity three-necked flask were added 4-{trans-4'-(hydroxymethyl)cyclohexyl}benzonitrile (75.6 g, 0.35 mol) and pyridine (150 ml), followed by cooling these down to 0° C., dropwise adding a pyridine solution (150 ml) of p-toluenesulfonyl chloride (70.3 g, 0.37 mol) over one hour, agitating these at room temperature for 2 hours, allowing them to stand overnight, adding water (500 ml), extracting with toluene, three times washing with water (300 ml), drying over magnesium sulfate, removing magnesium sulfate, concentrating the residue, passing it through a silica gel column using a chloroform solution, distilling off chloroform, recrystallizing from a mixed solvent of n-heptane with ethyl acetate and drying to obtain white crystals (103.5 g). The NMR spectra of this product accorded with those of the captioned compound and its M.P. was 108.1°-110.5° C.

Workup

  1. waitto stand overnight
  2. extractionextracting with toluene, three times
  3. washwashing with water (300 ml)
  4. dry with materialdrying over magnesium sulfate
  5. customremoving magnesium sulfate
  6. concentrationconcentrating the residue
  7. distillationdistilling off chloroform
  8. customrecrystallizing from a mixed solvent of n-heptane with ethyl acetate
  9. customdrying

Sources & evidence

ORD record
ord-9edfa593be8d435d97a73fe7dd976d06
Source dataset
uspto-grants-1993_04
Patent number
US05202055

Reaction notes

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