Reacción #2467048

Ecuación de reacción

sodium bicarbonate

diaminomethylenethiourea

Bromine

2-acetyl-6-cyanomethylpyridine

chloride

→

4-(6-cyanomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole

Rendimiento 46.5%

Disolventes

methanol

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred for 1 hour at 50° C
2. 2
   workup.STIRRINGthe mixture was stirred for 2.5 hours at 50° C
3. 3
   OtroThe solvent was removed by concentration in vacuo
4. 4
   workup.ADDITIONTo the residue was added
5. 5
   workup.ADDITIONa mixture of water, tetrahydrofuran and ethyl acetate
6. 6
   LavadoThe separated organic layer was washed with brine
7. 7
   Secadodried over magnesium sulfate
8. 8
   Otroevaporated in vacuo
9. 9
   OtroThe residue was triturated with water

Procedimiento

Bromine (0.64 ml) was added to a mixture of 2-acetyl-6-cyanomethylpyridine (2.0 g) in dioxane (30 ml) and 4N-dioxanichydrogen chloride (3.1 ml) at ambient temperature with stirring, and then the mixture was stirred for 1 hour at 50° C. To the mixture was added the sodium bicarbonate (5.2 g), methanol (30 ml) and diaminomethylenethiourea (2.2 g) at ambient temperature and the mixture was stirred for 2.5 hours at 50° C. The solvent was removed by concentration in vacuo. To the residue was added a mixture of water, tetrahydrofuran and ethyl acetate and the mixture was adjusted to pH 9.5 with potassium carbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with water to give 4-(6-cyanomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (1.5 g).

Fuente