Reaction #4447

Reaction equation

2-chloro-4-(4-pyridyl)thiazole

benzylcyanide

sodamide

→

2-phenyl-2-[4-(4-pyridyl)-2-thiazolyl]acetonitrile

Yield 8.3%

Solvents

toluene

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Otherthe mixture was quenched with water
3. 3
   Otherthe layers separated
4. 4
   Washthe aqueous phase washed with methylene chloride (2×50 mL)
5. 5
   DryingThe combined extracts were dried over sodium sulfate
6. 6
   Concentrationconcentrated
7. 7
   Otherchromatographed through silica gel (3:1 ethyl acetate/methylene chloride as eluant)
8. 8
   OtherAfter decolorizing with charcoal, recrystallization from hexane/ethyl acetate

Procedure

To a solution of 2-chloro-4-(4-pyridyl)thiazole (1.00 g, 0.005 mol) and benzylcyanide (1.18 g, 0.010 mol) in dry toluene (10 mL) at 5° C. was added sodamide (400 mg, 0.010 mol) and the mixture heated to 100° C. for 20 minutes. After cooling, the mixture was quenched with water, the layers separated, and the aqueous phase washed with methylene chloride (2×50 mL). The combined extracts were dried over sodium sulfate, concentrated, and chromatographed through silica gel (3:1 ethyl acetate/methylene chloride as eluant). After decolorizing with charcoal, recrystallization from hexane/ethyl acetate afforded 2-phenyl-2-[4-(4-pyridyl)-2-thiazolyl]acetonitrile (115 mg, 8%). mp. 110°-111° C.

Source