Thionyl Chloride → 4-(chloromethyl)-N-cyclopropylpyridine-2-carboxamide

HRID 714454Notes

Reaction equation

HRID 714454 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]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 59848863N-cyclopropyl-4-(hydroxymethyl)pyridine-2-carboxamide

Product 1

HCID 666314124-(chloromethyl)-N-cyclopropylpyridine-2-carboxamide

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

  1. concentrationThe reaction mixture was concentrated
  2. customa rotary evaporator
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed once with saturated aqueous sodium bicarbonate solution
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customa rotary evaporator
  9. customThe residue was purified by column chromatography on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 2/1)

Sources & evidence

ORD record
ord-62cf7e5595bb49c9ad538e15a1ea5daf
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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