Itaconic acid → 2-{[(1H-Benzimidazol-2-yl)sulfanyl]methyl}butanedioic acid

HRID 2226256Notes

Reaction equation

HRID 2226256 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C:11]([OH:19])(=[O:18])[C:12]([CH2:14][C:15]([OH:17])=[O:16])=[CH2:13].O.[OH-].[Na+]>OS(O)(=O)=O>[N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[NH:6][C:2]=1[S:1][CH2:13][CH:12]([C:11]([OH:19])=[O:18])[CH2:14][C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 811Itaconic acidHCID 962WaterHCID 14798Sodium HydroxideHCID 178527775HCID 178527775, compound

Product 1

HCID 194275062-{[(1H-Benzimidazol-2-yl)sulfanyl]methyl}butanedioic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

47.4 g of 2-mercaptobenzimidazole are reacted in the same manner as in Example 10 with 40.7 g of itaconic acid in 150 ml of 70% H2SO4 at 40°-43°. After dilution with water, sodium hydroxide solution is added until pH 4 is reached, the product being precipitated as the dihydrate. Anhydrous 3-(benzimidazol-2-ylthio)-propane-1,2-dicarboxylic acid, melting at 165°-168°, is obtained from the dihydrate by recrystallisation.

Workup

  1. customthe product being precipitated as the dihydrate

Sources & evidence

ORD record
ord-5ff7e027e8c1425a8bd071bf496de319
Source dataset
uspto-grants-1994_09
Patent number
US05347008

Reaction notes

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