N-bromobutanimide → HCID 53650041, compound

HRID 1281677Notes

Reaction equation

HRID 1281677 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:27][CH2:26][C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[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:28]=1.[Br:29]N1C(=O)CCC1=O>O1CCCC1>[Br:29][C:8]1[N:7]([C@@H:10]2[O:27][CH2:26][C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[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:28]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[N:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 69945486HCID 69945486, compound

Product 1

HCID 53650041HCID 53650041, compoundYield 129.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to General Procedure IV using 6-chloro-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.20 g, 0.41 mmol), 30 ml tetrahydrofuran (Aldrich Sure Seal, Milwaukee), and a total of 0.30 g (0.17 mmol) of N-bromosuccinimide that was added over 0.5 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-6-chloro-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.11 g, 0.22 mmol, 54%); MS (AP+): m/z (rel. intensity) 511 (0.10, M+23 (Na)) 1H NMR (DMSO-d6) δ8.16 (s,1H), 7.60-7.58 (d, 1H, J=8.7 Hz), 7.28-7.26 (dd, 1H, J=1.9 Hz, J=8.6 Hz), 5.95-5.92 (d, 1H, J=9.7 Hz), 5.67-5.60 (m, 3H), 4.13-4.09 (dd, 1H, J=5.3 Hz, J=9.2 Hz), 4.00-3.90 (overlapping dd, 1H) 2.20 (s, 3H), 1.98 (s, 3H), 1.74 (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-e30b588a58674671857c26168f740ea9
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

Loading…