Reaction #1583817

Reaction equation

sulphuric acid

N-benzyl-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine-2-amine

sodium hydroxide

→

4-[2-Ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine-2-amine

Solvents

Conditions

Workup

1. 1
   Extractionthe mixture is extracted with dichloromethane (3×100 ml)
2. 2
   DryingThe combined organic phases are dried over MgSO4
3. 3
   OtherThe residue is triturated with MTBE
4. 4
   Filtrationfiltered off
5. 5
   OtherThe product obtained

Procedure

With ice cooling, 23 ml of conc. sulphuric acid are added to 4.75 g (10.9 mmol) of N-benzyl-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine-2-amine, and the reaction mixture is stirred at room temperature for 30 min. The reaction mixture is stirred into 100 ml of ice-water, the pH is adjusted to 10 using concentrated aqueous sodium hydroxide solution and the mixture is extracted with dichloromethane (3×100 ml). The combined organic phases are dried over MgSO4 and freed from the solvent under reduced pressure. The residue is triturated with MTBE and filtered off. The product obtained is 2.80 g (82%) of a beige solid; log P (pH2.7): 1.29 with MS (ESI): 300.1 ([M+H]+).

Source