HCID 516035, compound → 6-Bromo-2,5-dichloro-1-beta-D-ribofuranosylbenzimidazole

HRID 727008Notes

Reaction equation

HRID 727008 reaction equation
[Cl:1][C:2]1[N:6]([C@@H:7]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[C:5]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:4]=2[N:3]=1.[Br:21]Br.O>O>[Br:21][C:17]1[C:18]([Cl:20])=[CH:19][C:4]2[N:3]=[C:2]([Cl:1])[N:6]([C@@H:7]3[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]3[OH:9])[C:5]=2[CH:16]=1

Participants

4

Reactant 2

HCID 516035HCID 516035, compoundHCID 86741833Bromine hydrate

Product 1

HCID 538231516-Bromo-2,5-dichloro-1-beta-D-ribofuranosylbenzimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 0.110 g (0.313 mmol, as C12H12Cl2 N2O 4MeOH) of 2,5-dichloro-1-β-D-ribofuranosylbenzimidazole (13) 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 (El) m/e 395.9274 (5% M+ =395.9279). 1H NMR (DMSO-d6): δ8.69 (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), (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.

Workup

  1. additionAfter the addition
  2. filtrationThe reaction mixture was filtered
  3. washthe solid was washed with portions of H2O
  4. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-bb44d4dce2254254bd1061d75fdf3684
Source dataset
uspto-grants-1998_01
Patent number
US05712255

Reaction notes

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