Reaction #710488

Reaction equation

sulfuric acid

N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethylidene}-2-(trifluoromethyl)benzamide

dichloromethane

water

→

desired product

Yield 63.0%

N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-1-methoxyethyl}-2-(trifluoromethyl)benzamide

Yield 63.0%

Solvents

methanol

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   OtherAfter separation
3. 3
   Extractionthe aqueous phase was extracted twice with dichloromethane
4. 4
   WashThe combined organic phases were washed with 5 mL of water
5. 5
   Dryingdried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   Otherto yield to 0.150 g of crude material, which
9. 9
   Otherwas purified by chromatography on silica gel

Procedure

0.16 g of N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethylidene}-2-(trifluoromethyl)benzamide (Int-6) were diluted in 2 mL of methanol. 50 μL of sulfuric acid 99% were added. The reaction mixture was stirred at room temperature for 48 hours. A mixture of dichloromethane (10 mL) and water (5 mL) was added. After separation, the aqueous phase was extracted twice with dichloromethane. The combined organic phases were washed with 5 mL of water, dried over magnesium sulfate, filtered, concentrated to yield to 0.150 g of crude material, which was purified by chromatography on silica gel to yield 0.107 g (63%) of desired product N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-1-methoxyethyl}-2-(trifluoromethyl)benzamide (Ia-111), [M+1]=427.

Source