反応 #2063065

反応方程式

1-bromo-4-chlorobutane

Sodium hydride

N-phenyl-2-benzothiazolamine

→

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

収率 66.0%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   その他prepared
2. 2
   その他the resulting reaction mixture
3. 3
   workup.STIRRINGwas stirred
4. 4
   温度refluxed for 48 hours
5. 5
   温度The mixture was cooled
6. 6
   その他the solvent was evaporated
7. 7
   その他The residue was partitioned between water and CH2Cl2
8. 8
   その他The organic layer was separated
9. 9
   その他dried
10. 10
    ろ過filtered
11. 11
    その他the solvent evaporated
12. 12
    その他The residue was purified by column chromatography over silica gel (eluent: CH2Cl2)
13. 13
    その他The desired fractions were collected
14. 14
    その他the solvent was evaporated

実験手順

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.

出典