Dicyclohexylcarbodiimide → HCID 19992017, compound

HRID 345291Notes

Reaction equation

HRID 345291 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[Cl:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][N:18]=1.O[CH2:27][C:28]1([CH2:32][CH2:33][CH3:34])[CH2:31][O:30][CH2:29]1>CN(C)C=O>[Cl:16][C:17]1[N:18]=[CH:19][C:20]([C:21]([O:23][CH2:27][C:28]2([CH2:32][CH2:33][CH3:34])[CH2:31][O:30][CH2:29]2)=[O:22])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 792226-Chloronicotinic acidHCID 1838902-Propyl-2-oxetanemethanol

Product 1

HCID 19992017HCID 19992017, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of dicyclohexylcarbodiimide (2.0 gm.) in dry dimethylformamide (5 ml.) was added to a stirred solution of 6-chloronicotinic acid and 3 -hydroxymethyl-3-n-propyloxetane in dry dimethylformamide (15 ml.) at room temperature. The reaction mixture was stirred at room temperature for 60 hours. The mixture was filtered and the solid was washed with diethyl ether (50 ml.). The filtrates were washed with water and then with 5% aqueous sodium carbonate solution. The etheral solution was washed with brine and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo. The residue was purified by chromatography on silica, eluting with 1% triethylamine:chloroform. (3-n-propyl-oxetan-3-yl)methyl 6-chloro-3-pyridinecarboxylate was obtained as an oil, which solidified on standing (289 mg.).

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with diethyl ether (50 ml.)
  3. washThe filtrates were washed with water
  4. washThe etheral solution was washed with brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customThe solvent was removed in vacuo
  7. customThe residue was purified by chromatography on silica
  8. washeluting with 1% triethylamine

Sources & evidence

ORD record
ord-821dc08f5a70461baffe687a9da1c92d
Source dataset
uspto-grants-1991_10
Patent number
US05057504

Reaction notes

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