N-bromobutanimide → HCID 54518783, compound

HRID 1167077Notes

Reaction equation

[Cl:1][C:2]1[C:28]([Cl:29])=[CH:27][C:5]2[N:6]([C@H:9]3[O:21][C@@H:20]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@@H:10]3[O:11][C:12](=[O:14])[CH3:13])[CH:7]=[N:8][C:4]=2[CH:3]=1.[Br:30]N1C(=O)CCC1=O>O1CCOCC1.C(OCC)(=O)C>[Br:30][C:7]1[N:6]([C@H:9]2[O:21][C@@H:20]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@@H:10]2[O:11][C:12](=[O:14])[CH3:13])[C:5]2[CH:27]=[C:28]([Cl:29])[C:2]([Cl:1])=[CH:3][C:4]=2[N:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

5,6-Dichloro-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazole (1.0 g, 2.25 mmol) was combined with N-bromosuccinimide (0.88 g 4.94 mmol) in anhydrous 1,4-dioxane (50 mL). This solution was heated in an 80° C. oil bath for 15 min. The solution was cooled, diluted with ethyl acetate and extracted with 10% sodium bicarbonate (2×50 mL). The organics were dried with anhydrous Na2SO4, decanted and concentrated. The residue was purified on a silica gel column (5×11 cm, 230-400 mesh) with (1:50) methanol:dichloromethane to give a white solid which was identified as product by comparing it's 1H NMR to that of Example 1.

Workup

temperatureThe solution was cooled
extractionextracted with 10% sodium bicarbonate (2×50 mL)
dry with materialThe organics were dried with anhydrous Na2SO4
customdecanted
concentrationconcentrated
customThe residue was purified on a silica gel column (5×11 cm, 230-400 mesh) with (1:50) methanol
customdichloromethane to give a white solid which

Sources & evidence

ORD record: ord-6c1775d161724625a71d655c2bde920d
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06617315B1

Reaction notes

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