تفاعل #2063065

معادلة التفاعل

1-bromo-4-chlorobutane

Sodium hydride

N-phenyl-2-benzothiazolamine

→

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

المردود 66.0%

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىprepared
2. 2
   أخرىthe resulting reaction mixture
3. 3
   workup.STIRRINGwas stirred
4. 4
   درجة الحرارةrefluxed for 48 hours
5. 5
   درجة الحرارةThe mixture was cooled
6. 6
   أخرىthe solvent was evaporated
7. 7
   أخرىThe residue was partitioned between water and CH2Cl2
8. 8
   أخرىThe organic layer was separated
9. 9
   أخرىdried
10. 10
    ترشيحfiltered
11. 11
    أخرىthe solvent evaporated
12. 12
    أخرىThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2)
13. 13
    أخرىThe desired fractions were collected
14. 14
    أخرىthe solvent was evaporated

الإجراء التجريبي

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.

المصدر