Reaktion #2063065

Reaktionsgleichung

1-bromo-4-chlorobutane

Sodium hydride

N-phenyl-2-benzothiazolamine

→

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

Ausbeute 66.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   Sonstigethe resulting reaction mixture
3. 3
   workup.STIRRINGwas stirred
4. 4
   Temperaturrefluxed for 48 hours
5. 5
   TemperaturThe mixture was cooled
6. 6
   Sonstigethe solvent was evaporated
7. 7
   SonstigeThe residue was partitioned between water and CH2Cl2
8. 8
   SonstigeThe organic layer was separated
9. 9
   Sonstigedried
10. 10
    Filtrationfiltered
11. 11
    Sonstigethe solvent evaporated
12. 12
    SonstigeThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2)
13. 13
    SonstigeThe desired fractions were collected
14. 14
    Sonstigethe solvent was evaporated

Vorschrift

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.

Quelle