Carbon Tetrachloride → 5-Chloro-2-methoxy-3-pyridinecarbonyl chloride
Reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(Cl)(Cl)(Cl)[Cl:14].S(Cl)(Cl)=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([Cl:14])=[O:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 3.76 g. (0.02 mole) of 5-chloro-2-methoxynicotinic acid in 100 ml. of carbon tetrachloride, there were added 100 ml. of thionyl chloride in one portion and the resulting mixture was then refluxed on a steam bath for a period of 90 minutes. Upon completion of this step, the clear solution so obtained was cooled and then concentrated in vacuo at room temperature to afford a residual oil. The excess thionyl chloride present was next removed in the same manner as described in Preparation A for the production of 2-methoxynicotinoyl chloride, except that only 100 ml. of benzene was employed this time (i.e., during each purification step). The yield of pure 5-chloro-2-methoxynicotinoyl chloride, obtained as the residual product, was quantitative in this particular instance.
Workup
- additionTo a suspension of 3.76 g
- customUpon completion of this step, the clear solution so obtained
- temperaturewas cooled
- concentrationconcentrated in vacuo at room temperature
- customto afford a residual oil
- customThe excess thionyl chloride present was next removed in the same manner
- customas described in Preparation A for the production of 2-methoxynicotinoyl chloride, except that only 100 ml
- customduring each purification step)
Sources & evidence
- ORD record
- ord-da49a25e91114e4d8907dd163c963add
- Source dataset
- uspto-grants-1976_06
- Patent number
- US03961065
Reaction notes
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