N-bromobutanimide → HCID 54506767, compound

HRID 1281675Notes

Reaction equation

HRID 1281675 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]([C@@H:9]3[O:26][CH2:25][C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[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:29]N1C(=O)CCC1=O>O1CCCC1>[Br:29][C:7]1[N:6]([C@@H:9]2[O:26][CH2:25][C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[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]=[CH:28][C:2]([Cl:1])=[CH:3][C:4]=2[N:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 69944453HCID 69944453, compound

Product 1

HCID 54506767HCID 54506767, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to General Procedure IV using 5-chloro-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.17 g, 0.41 mmol), 30 ml tetrahydrofuran (Aldrich Sure Seal, Milwaukee), and a total of 2.6 g (7.0 mmol) of N-bromosuccinimide that was added over 2 h. The product from work-up by General Procedure IV was purified on a silica gel column (2.5×20 cm, 230-400 mesh) with dichloromethane containing 1.0% methanol to give 2-Bromo-5-chloro-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.15 g, 0.31 mmol, 76%); MS (ES+): m/z (rel. intensity) 511 (0.25, M+23 (Na)) 1H NMR (DMSO-d6) δ8.02-8.00 (d,1H, J=8.7), 7.68 (d, 1H, J=2.1 Hz), 7.30-7.27 (dd, 1H, J=1.9 Hz, J=8.9 Hz), 5.96-5.93 (d, 1H, J=8.9 Hz), 5.67-5.62 (m, 2H), 5.55-5.45 (m,1H), 4.20-3.90 (m, 2H), 2.20 (s, 3H), 1.99 (s, 3H), 1.73 (s, 3H).

Workup

  1. customThe title compound was prepared
  2. customThe product from work-up by General Procedure IV was purified on a silica gel column (2.5×20 cm, 230-400 mesh) with dichloromethane containing 1.0% methanol

Sources & evidence

ORD record
ord-a1c2f3e03ce349d1948d8f28c3f7c450
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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