Reacción #63728

Ecuación de reacción

potassium carbonate

2-chloromethyl-3 -methyl-4-nitropyridine

5,7-dihydro-2-mercapto-5,5,7,7-tetramethylindeno[5,6-d]-imidazol-6(1H)-one

→

5,7-dihydro-5,5,7,7-tetramethyl-2 -[[(3-methyl-4-nitro-2 -pyridyl)methyl]thio]indeno[5,6-d]imidazol-6(1H)-one

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISTILLATION100 ml of acetone are distilled off in vacuo, whereupon the residue
2. 2
   workup.ADDITIONis poured on to ice
3. 3
   OtroThe product which crystallizes out
4. 4
   Filtraciónis filtered off
5. 5
   workup.DISSOLUTIONdissolved in methylene chloride
6. 6
   Otrothe solution obtained
7. 7
   Lavadois washed with water
8. 8
   Otrodried
9. 9
   Concentraciónconcentrated
10. 10
    OtroBy recrystallization from ethyl acetate/ether there

Procedimiento

A solution of 11,5 g (0.062 mol) of 2-chloromethyl-3 -methyl-4-nitropyridine and 16 g (0.06 mol) of 5,7-dihydro-2-mercapto-5,5,7,7-tetramethylindeno[5,6-d]-imidazol-6(1H)-one in 200 ml of abs. acetone is treated with 13 g of finely ground potassium carbonate and the mixture is stirred at room temperature under argon for 18 hours, 100 ml of acetone are distilled off in vacuo, whereupon the residue is poured on to ice. The product which crystallizes out is filtered off and dissolved in methylene chloride; the solution obtained is washed with water, dried and concentrated. By recrystallization from ethyl acetate/ether there is obtained 5,7-dihydro-5,5,7,7-tetramethyl-2 -[[(3-methyl-4-nitro-2 -pyridyl)methyl]thio]indeno[5,6-d]imidazol-6(1H)-one of melting point 181°-183° (decomposition).

Fuente