Ethanol → 2-Bromo-5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole

HRID 2227222Notes

Reaction equation

HRID 2227222 reaction equation
C([O-])([O-])=O.[Na+].[Na+].CCO.CO.[Br:12][C:13]1[N:17]([C@@H:18]2[O:30][C@H:29]([CH3:31])[C@@H:24]([O:25]C(=O)C)[C@H:19]2[O:20]C(=O)C)[C:16]2[CH:32]=[C:33]([Cl:37])[C:34]([Cl:36])=[CH:35][C:15]=2[N:14]=1>O.CC(O)=O>[Br:12][C:13]1[N:17]([C@@H:18]2[O:30][C@H:29]([CH3:31])[C@@H:24]([OH:25])[C@H:19]2[OH:20])[C:16]2[CH:32]=[C:33]([Cl:37])[C:34]([Cl:36])=[CH:35][C:15]=2[N:14]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 10340Sodium CarbonateHCID 699962602-Bromo-5,6-dichloro-1-(5-deoxy-2,3-di-O-acetyl-beta-D-ribofuranosyl)benzimidazole

Product 1

HCID 5129192-Bromo-5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazoleYield 61%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred solution of Na2CO3 (0.325 g, 3 mmol) in H2O (10 mL), were added successively 45 mL of EtOH, 45 mL of MeOH, and 0.46 g (1 mmol) of 2b. Stirring was continued at room temperature for 2 h. The reaction mixture was neutralized with glacial AcOH and then concentrated to about 10 mL. The yellow, oily residue was triturated with H2O (10 mL) and the resulting yellow precipitate was collected by filtration. This precipitate was dissolved in EtOH, decolorized with charcoal, and recrystallized from H2O/EtOH/dioxane. Final recrystallization from H2O gave 0.206 g (61 %) of 4a. MP: 85-86° C. MS: (EI, with DCI probe) m/z 336 (4, M+=336). 1H NMR (DMSO-d6): δ7.99 (s, 1, 4-H), 7.89 (s, 1, 7-H), 5.87 (d, 1, 1-H, J1′-2′=6.5 Hz), 5.53 (d, 1, 2′-OH, J2′-2′=6.0 Hz), 5.28 (d, 1, 3′-OH, J3′-3′OH=5.0 Hz), 4.49 (m, 1, 2′-H, J2′-3′=6.0 Hz), 4.00 (M, 1, 4′-H, J3′-4′=4.0 Hz, J4′-5′=6.5 Hz), 3.89 (m, 1, 3′-H), 1.41 (d, 3, 5′-H). 13C NMR (DMSO-d6): δ142.09 (C2), 141.03 (C3a), 132.68 (C7a), 126.14, 125.93 (C5 and C6), 120.40 (C4), 113.42 (C7), 90.02 (C1′), 80.97 (C4′), 73.80 (C3′), 71.71 (C2′), 18.88 (C5′). Anal. (C12H11Cl3N2O3) C, H, N.

Workup

  1. concentrationconcentrated to about 10 mL
  2. customThe yellow, oily residue was triturated with H2O (10 mL)
  3. filtrationthe resulting yellow precipitate was collected by filtration
  4. dissolutionThis precipitate was dissolved in EtOH
  5. customrecrystallized from H2O/EtOH/dioxane
  6. customFinal recrystallization from H2O

Sources & evidence

ORD record
ord-e024f27c7fd14b0e91e9d42568b42e43
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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