Reacción #2063065

Ecuación de reacción

1-bromo-4-chlorobutane

Sodium hydride

N-phenyl-2-benzothiazolamine

→

N-(4-chlorobutyl)-N-phenyl-2-benzothiazolamine

Rendimiento 66.0%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprepared
2. 2
   Otrothe resulting reaction mixture
3. 3
   workup.STIRRINGwas stirred
4. 4
   Temperaturarefluxed for 48 hours
5. 5
   TemperaturaThe mixture was cooled
6. 6
   Otrothe solvent was evaporated
7. 7
   OtroThe residue was partitioned between water and CH2Cl2
8. 8
   OtroThe organic layer was separated
9. 9
   Otrodried
10. 10
    Filtraciónfiltered
11. 11
    Otrothe solvent evaporated
12. 12
    OtroThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2)
13. 13
    OtroThe desired fractions were collected
14. 14
    Otrothe solvent was evaporated

Procedimiento

Sodium hydride (0.05 mol) was added portionwise to a solution of N-phenyl-2-benzothiazolamine, prepared according to the procedure described in J. Chem. Soc, 1962, 230, (0.05 mol) in tetrahydrofuran (200 ml). The mixture was stirred for 15 minutes. A solution of 1-bromo-4-chlorobutane (0.05 mol) in tetrahydrofuran (50 ml) was added dropwise and the resulting reaction mixture was stirred and refluxed for 48 hours. The mixture was cooled, and the solvent was evaporated. The residue was partitioned between water and CH2Cl2. The organic layer was separated, dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2). The desired fractions were collected and the solvent was evaporated, yielding 10.4 g (66%) of N-(4-chlorobutyl)-N-phenyl-2-benzothiazolamine (interm. 10). N-(5-chloropentyl)-N-phenyl-2-benzothiazolamine (interm. 24) was prepared similarly.

Fuente