Sodium Carbonate → HCID 54160477, compound

HRID 1281698Notes

Reaction equation

HRID 1281698 reaction equation
[Br:1][C:2]1[N:6]([C@@H:7]2[O:24][CH2:23][C@H:18]([O:19]C(=O)C)[C@@H:13]([O:14]C(=O)C)[C@@H:8]2[O:9]C(=O)C)[C:5]2[CH:25]=[C:26]([Cl:30])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[Br:1][C:2]1[N:6]([C@H:7]2[O:24][CH2:23][C@H:18]([OH:19])[C@@H:13]([OH:14])[C@@H:8]2[OH:9])[C:5]2[CH:25]=[C:26]([Cl:30])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 53919134HCID 53919134, compound

Product 1

HCID 54160477HCID 54160477, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An ethanolic solution of 2-bromo-5,6-dichloro-1-(2,3,4-tri-O-acetyl-alpha-L-xylopyranosyl)-1H-benzimidazole (0.81 g, 1.54 mmol) was deprotected in a modification of General Procedure VI with 0.64 g (6.03 mmol) of sodium carbonate in 5 ml of water. After stirring overnight at ambient temperature, the mixture was treated as described in General Procedure VI to give crude product which was recrystallized from 1-chlorobutane, ethyl acetate and hexane to give 0.21 g (0.53 mmol, 34% yield) of 2-bromo-5,6-dichloro-1-beta-L-xylopyranosyl-1H-benzimidazole, mp 164-165° C. 1H NMR (CD3OD) δ8.04 (s,1H), 7.83 (s, 1H), 5.53-5.50 (d, 1H), 4.14-4.09 (dd, 1H), 3.93 (bm, 1H), 3.83-3.75 (m, 1H), 3.55-3.46 (m, 2H).

Workup

  1. additionthe mixture was treated
  2. customto give crude product which
  3. customwas recrystallized from 1-chlorobutane, ethyl acetate and hexane

Sources & evidence

ORD record
ord-c07835b42fa643ea8d81b0955c336c08
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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