Dimethylformamide → HCID 178497635, compound

HRID 916085Notes

Reaction equation

HRID 916085 reaction equation
[H-].[Na+].CN(C)C=O.[CH3:8][O:9][C:10](=[O:28])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][S:18][C:19]1[NH:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1.[C:29]([O:33][C:34](=[O:37])[CH2:35]Br)([CH3:32])([CH3:31])[CH3:30]>O>[C:29]([O:33][C:34](=[O:37])[CH2:35][C:27]1[C:21]2[NH:20][C:19]([S:18][CH2:17][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10]([O:9][CH3:8])=[O:28])=[N:23][C:22]=2[CH:24]=[CH:25][CH:26]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 69456394HCID 69456394, compound

Product 1

HCID 178497635HCID 178497635, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydride (400 mg, 10.0 mmol) and dimethylformamide (30 ml) were added to a previously dried reaction vessel. To the mixture were added 2-(benzimidazole-2-ylthiomethyl)benzoic acid methyl ester (1500 mg, 5.0 mmol) and bromoacetate t-butyl ester (1463 mg, 7.5 mmol), and the mixture was stirred at 80° C. for 2 hours. Water was added thereto, followed by extraction with ether. After the ether phase was dried with anhydrous sodium sulfate, it was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 2-(2-((2-(methoxycarbonyl)phenyl)methylthio)benzimidazolyl)acetic acid t-butyl ester (1298 mg, yield 63%).

Workup

  1. extractionfollowed by extraction with ether
  2. dry with materialAfter the ether phase was dried with anhydrous sodium sulfate, it
  3. concentrationwas concentrated
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-30f3d3bdd2904bb7b0477e9673818adf
Source dataset
uspto-grants-2007_09
Patent number
US07268145B2

Reaction notes

Loading…