반응 #351046

반응 방정식

2,5-dichloro-1-β-D-ribofuranosylbenzimidazole

Br2 H2O

→

99

6-Bromo-2,5-dichloro-1-β-D-ribofuranosylbenzimidazole

용매

H2O

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the addition
2. 2
   여과The reaction mixture was filtered
3. 3
   세척the solid was washed with portions of H2O
4. 4
   기타recrystallized from MeOH

실험 절차

To a suspension of 0.110 g (0.313 mmol, as C12H12Cl2N2O4MeOH) of 2,5-dichloro-1-β-D-ribofuranosylbenzimidazole (73) in 3 mL of H2O was added dropwise 10 mL of a sat. solution of Br2/H2O at room temperature. After the addition had been completed, stirring was continued for 6 hr. The reaction mixture was filtered and the solid was washed with portions of H2O, and then recrystallized from MeOH to give 0.091 g (73%, 2 crops) of 99 as white crystalline needles. MP 158°-159° C. MS (EI) m/e 395.9274 (5% M+ =395.9279). 1H NMR (DMSO-d6): δ 8.69 (s, 1, 7-H), 7.96 (s, 1, 4-H), 5.88 (d, 1, 1'-H, J1'-2' =8.0 Hz), 5.51 (d, 1, 2'-OH, J2'-2'OH =6.5 Hz), 5.41 (t, 5'-OH, J5'-5'OH =4.5 Hz), 5.30 (d, 1, 3'-OH, J3'-3'OH =4.5 Hz), 4.42 (m, 1, 2'-H, J2'-3' =5.5 Hz), 5.30 (d, 1, 3'-OH, J3'-4' =1.5 Hz), 4.01 (m, 1, 4'-H, J4'-5' =J4'-5'=2.5 Hz), 371 (m, 2, 5'-H, and 5"-H, J5'-5" =1.20 Hz). Anal. Calcd. for C12H11BrCl2N2O4 : C, 36.21; H, 2.79; N, 7.04. Found: C, 36.14; H, 2.90; N, 6.90.

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