HCID 516036, compound → 5-Bromo-2,6-dichloro-1-beta-D-ribofuranosylbenzimidazole

HRID 6350Notes

Reaction equation

HRID 6350 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]=[C:17]([Cl:20])[CH:18]=[CH:19][C:4]=2[N:3]=1.[Br:21]Br.O>O>[Br:21][C:18]1[C:17]([Cl:20])=[CH:16][C:5]2[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:2]([Cl:1])=[N:3][C:4]=2[CH:19]=1

Participants

4

Reactant 2

HCID 516036HCID 516036, compoundHCID 86741833Bromine hydrate

Product 1

HCID 538729035-Bromo-2,6-dichloro-1-beta-D-ribofuranosylbenzimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 0.319 g (1.0 mmol) of 2,6-dichloro-1-β-D-ribofuranosylbenzimidazole in 10 mL of H2O, was added dropwise a sat. solution of Br2 /H2O at room temperature. After the addition has been completed, stirring was continued for 3 h. The reaction mixture was filtered and the solid was washed with portions of H2O, and then recrystallized from MeOH to give 0.335 g (78%, as M MeOH) of 95 as white crystalline needles. MP 140°-142° C. MS (El) m/e 395.9274 (2%, M+ =395.9279). 1H NMR (DMSO-d6): δ8.88 (s, 1, 7-H), 8.08 (s, 1, 4-H), 5.89 (d, 1, 1'-H, J1'-2' =8.0 Hz), 5.49 (d, 1, 2'-OH, J2'-2'OH =6.5 Hz), 5.40 (t, 5'-OH, J5'-5'OH =4.0 Hz), 5.28 (d, 1, 3'-OH, J3'-3'OH =4.5 HZ), 4.42 (m, 1, 2'-H, J2'-3' =5.5 Hz), 4.13 (m, 1, 3'-H, J3'-4' =1.5 Hz), 4.01 (m, 1, 4'-H, J4'-5' =J4'-5" =2.5 Hz), 3.70 (m, 2, 5'-H and 5"-H, J5'-5" =12.0 Hz). Anal. Calcd. for C12H11BrCl2N2O4MeOH: C, 36.30; H, 3.51; N, 6.51. Found: C, 35.98; H, 3.60; N, 6.39.

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-970b971bcff641f38c1bdbadc4189929
Source dataset
uspto-grants-1993_09
Patent number
US05248672

Reaction notes

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