Chloroform → HCID 70177980, compound

HRID 2227199Notes

Reaction equation

HRID 2227199 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C@@H:10]3[O:22][C@H:21]([CH3:23])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]3[O:12][C:13](=[O:15])[CH3:14])[C:6]=2[CH:24]=1.[Br:25]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+].C(Cl)(Cl)Cl>C1COCC1>[Br:25][C:8]1[N:7]([C@@H:10]2[O:22][C@H:21]([CH3:23])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]2[O:12][C:13](=[O:15])[CH3:14])[C:6]2[CH:24]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[N:9]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 22086279HCID 22086279, compound

Product 1

HCID 70177980HCID 70177980, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a refluxing solution of 0.76 g (2.2 mmol) of 6-chloro-1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole in 30 mL of THF was added 0.77 g (4.3 mmol) of N-bromosuccinimide. The resultant mixture was further refluxed for 15 min. The reaction mixture was then poured into an ice-cooled mixture of 20 mL sat. NaHCO3 solution and 20 mL CHCl3. The CHCl3 layer was separated and was further washed with sat. NaHCO3. After drying (MgSO4) and solvent removal, a crude product was obtained which was purified by flash column chromatography on silica with EtOAc/hexane (2:3) as the eluent. This gave 0.73 g (79%) of the title compound as an oil. 1H NMR (DMSO-d6) δ1.42 (d, 3H, CH3), 2 (s, 3H, COCH3), 2.1 (s, 3H, COCH3), 4.2 (quintet, 1H, CH), 5.2 (t, 1H, CH), 5.6 (t, 1H, CH), 6.1 (d, 1H, CH), 7.3 (d, 1H, aromatic), 7.6 (d, 1H, aromatic), 7.82 (s, 1H, aromatic).

Workup

  1. temperaturecooled
  2. customThe CHCl3 layer was separated
  3. washwas further washed with sat. NaHCO3
  4. customAfter drying
  5. custom(MgSO4) and solvent removal

Sources & evidence

ORD record
ord-c32aa048b869425d99771da3be3aced9
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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