Thionyl Chloride → 2-(CYCLOPROPYLAMINO)-3-PYRIDINECARBONYL CHLORIDE

HRID 1840629Notes

Reaction equation

HRID 1840629 reaction equation
S(Cl)([Cl:3])=O.[CH:5]1([NH:8][C:9]2[C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:7][CH2:6]1>C(#N)C>[CH:5]1([NH:8][C:9]2[C:14]([C:15]([Cl:3])=[O:17])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 100351632-CYCLOPROPYLAMINONICOTINIC ACID

Product 1

HCID 103754462-(CYCLOPROPYLAMINO)-3-PYRIDINECARBONYL CHLORIDE

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Thionyl chloride (25 ml, 40.8 g, 0.343 mol) was charged in a thin stream to 9.00 g, 0.048 mol, of 2-(cyclopropylamino)-3-pyridine carboxylic acid from Example 2 in acetonitrile. The mixture was heated at reflux temperature for 30 minutes. The mixture was allowed to cool and the thionyl chloride was distilled off at 40° C./23 in. Hg until the pot contents became thick. Toluene (25 ml) was added and distillation of thionyl chloride and toluene at 40° C. was continued until about one-half of the liquid was distilled. The remaining solution was allowed to cool and stirred to promote crystallization. Heptane (25 ml) was added to the mixture with stirring and the mixture filtered under a nitrogen atmosphere to obtain the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 30 minutes
  3. temperatureto cool
  4. distillationthe thionyl chloride was distilled off at 40° C./23 in
  5. additionToluene (25 ml) was added
  6. distillationdistillation of thionyl chloride and toluene at 40° C.
  7. distillationwas distilled
  8. temperatureto cool
  9. customcrystallization
  10. additionHeptane (25 ml) was added to the mixture
  11. stirringwith stirring
  12. filtrationthe mixture filtered under a nitrogen atmosphere

Sources & evidence

ORD record
ord-781b933a8cb74dc08223ac9719a5cea8
Source dataset
uspto-grants-2004_01
Patent number
US06680383B1

Reaction notes

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