Thionyl Chloride → 4-(chloromethyl)-N-cyclopropylpyridine-2-carboxamide
Reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:12]=[C:11]([CH2:13]O)[CH:10]=[CH:9][N:8]=2)=[O:6])[CH2:3][CH2:2]1.S(Cl)([Cl:17])=O>>[Cl:17][CH2:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([C:5]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[O:6])[CH:12]=1Participants
3
Procedure
2.5 g (13.01 mmol) of N-cyclopropyl-4-(hydroxymethyl)pyridine-2-carboxamide (Example 52A) and 11.76 g (98.84 mmol) of thionyl chloride were combined and stirred at RT overnight. The reaction mixture was concentrated using a rotary evaporator. The residue was dissolved in ethyl acetate and washed once with saturated aqueous sodium bicarbonate solution. The organic phase was dried over magnesium sulfate, filtered and concentrated using a rotary evaporator. The residue was purified by column chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 2/1).
Workup
- concentrationThe reaction mixture was concentrated
- custom