Water → HCID 57595851, compound

HRID 1785480Notes

Reaction equation

HRID 1785480 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:6]2[NH:7][CH:8]=[N:9][C:5]=2[CH:4]=1.[H-].[Na+].[CH3:16][O:17][C:18]([C:20]1[S:24][C:23](Br)=[N:22][C:21]=1[Br:26])=[O:19].O>CN1CCCC1=O>[CH3:16][O:17][C:18]([C:20]1[S:24][C:23]([N:9]2[C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[CH:10][C:6]=3[N:7]=[CH:8]2)=[N:22][C:21]=1[Br:26])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 6012215,6-DimethoxybenzimidazoleHCID 46311119Methyl 2,4-dibromo-1,3-thiazole-5-carboxylate

Product 1

HCID 57595851HCID 57595851, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 5,6-Dimethoxy-1H-benzimidazole (1.0 g, 5.65 mmol) in 1-methyl-2-pyrrolidinone (10 ml) at 0° C. was added NaH (60% dispersion; 339 mg, 8.475 mmol). After gas evolution had stopped, 2,4-Dibromo-thiazole-5-carboxylic acid methyl ester (1.7 g, 5.65 mmol) was added. The resulting solution was stirred at ambient temperature for 1 hr. 50 ml water was added. The suspension was stirred for 10 min and filtered to afford 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (1.6 g, 73%) as a light brown solid. 1H NMR (300 MHz, CDCl3) δ 3.96 (s, 3H), 3.98 (s, 3H), 4.03 (s, 3H), 7.32 (s, 1H), 7.58 (s, 1H), 8.39 (s, 1H).

Workup

  1. stirringThe suspension was stirred for 10 min
  2. filtrationfiltered

Sources & evidence

ORD record
ord-342d8b1c96644769bb9b2301fe33859a
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

Loading…