Dichloromethane → 3-Isocyanatopyridine

HRID 1384995Notes

Reaction equation

HRID 1384995 reaction equation
Cl.C(O)(=O)[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.C(Cl)Cl.[C:14](Cl)(=[O:18])C(Cl)=O.[N-:20]=[N+]=[N-].[Na+]>C1(C)C=CC=CC=1>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([N:20]=[C:14]=[O:18])[CH:4]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 33557Sodium AzideHCID 65578Oxalyl chlorideHCID 715583-Pyridinecarboxylic acid, hydrochloride

Product 1

HCID 27604933-Isocyanatopyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Nicotinic acid hydrochloride (296 mg, 2.40 mmol) was suspended with 2 ml of methylene chloride and 2 ml of oxalic chloride was added and refluxed with stirring for 3 hours, then concentrated in reduced pressure. Residue was suspended with 10 ml of toluene and sodiumazide (468 mg, 7.2 mmol) was added and refluxed with stirring for 1 night to form 3-pyridylisocyanate. Methyl (1S,8S,12S)-2-aminomethyl-4,4-dimethyl-3,5,11-trioxa-12-benzyloxy-tricyclo[6.4.0.0<2,6>] dodec-9-en-9-carboxylate was added to above obtaind solution, and 2 ml of pyridine was added drop by drop and stirred for 2 hours at room temperature. Ethylacetate was added to reaction mixture and washed with saturated sodium bicarbonate and saturated saline solution. After drying and concentrating with anhydrous magnesium sulfate, residue was purified by using silica gel column chromatography (hexane/ethylacetate=2/1, v/v), and 550 mg of captioned compound was obtained (yield: 90%).

Workup

  1. additionwas added
  2. temperaturerefluxed
  3. concentrationconcentrated in reduced pressure
  4. additionwas added
  5. temperaturerefluxed
  6. stirringwith stirring for 1 night

Sources & evidence

ORD record
ord-9491770b6da545e480c2419559518ddf
Source dataset
uspto-grants-2001_07
Patent number
US06262083B1

Reaction notes

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