Reaction #710477

Reaction equation

water

1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride

triethylamine

trichloroacetyl chloride

water

→

2,2,2-trichloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-acetamide

Yield 62.0%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Otherthe reaction and liquid separation
2. 2
   WashThe organic layer was washed once with water and twice with 1% hydrochloric acid
3. 3
   Dryingdried over anhydrous magnesium sulfate
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   workup.ADDITIONDiethyl ether was added
6. 6
   Otherto precipitate a solid
7. 7
   Otherthus the solid was collected
8. 8
   Otherdried
9. 9
   Otherto obtain the subject material
10. 10
    OtherAmount obtained 61 mg (yield 62%)

Procedure

70 mg (0.27 mmol) of the 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride obtained by the method described in another method of Synthetic Example P1 was dissolved in 4 ml of anhydrous dichloromethane, 94 μl (0.68 mmol, 68 mg) of triethylamine and 33 g (0.27 mmol, 49 mg) of trichloroacetyl chloride were added thereto in sequence, and the resulting mixture was stirred at room temperature for 1 hour. After the reaction was completed, water was added thereto to stop the reaction and liquid separation was performed with dichloromethane and water. The organic layer was washed once with water and twice with 1% hydrochloric acid, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected and dried to obtain the subject material. Amount obtained 61 mg (yield 62%).

Source