반응 #2063065

반응 방정식

1-bromo-4-chlorobutane

Sodium hydride

N-phenyl-2-benzothiazolamine

→

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

수율 66.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타prepared
2. 2
   기타the resulting reaction mixture
3. 3
   workup.STIRRINGwas stirred
4. 4
   온도refluxed for 48 hours
5. 5
   온도The mixture was cooled
6. 6
   기타the solvent was evaporated
7. 7
   기타The residue was partitioned between water and CH2Cl2
8. 8
   기타The organic layer was separated
9. 9
   기타dried
10. 10
    여과filtered
11. 11
    기타the solvent evaporated
12. 12
    기타The residue was purified by column chromatography over silica gel (eluent: CH2Cl2)
13. 13
    기타The desired fractions were collected
14. 14
    기타the solvent was evaporated

실험 절차

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.

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