Methanol → HCID 178497357, compound

Reaction equation

[Cl:1][CH2:2][C:3]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([C:12]([OH:14])=[O:13])=[CH:11][C:5]=2[N:4]=1.S(=O)(=O)(O)O.[CH3:20]O>>[Cl:1][CH2:2][C:3]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([C:12]([O:14][CH3:20])=[O:13])=[CH:11][C:5]=2[N:4]=1

Participants

Reactant 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 178524165HCID 178524165, compound

Product 1

HCID 178497357HCID 178497357, compoundYield 71%

Procedure

To 2-(Chloromethyl)-1H-benzimidazole-5-carboxylic acid (4) (0.5 g; 2.4 mmole) suspended in anhydrous methanol (20 ml) was added dropwise Sulfuric acid (0.2 ml). The reaction mixture was maintained at reflux for 16 hours. The solvent was evaporated to give the crude oily product, which was purified by column chromatography (silica, 10% methanol: dichloromethane) to obtain 0.4 g (71% yield) of product 5.

Workup

temperatureThe reaction mixture was maintained
temperatureat reflux for 16 hours
customThe solvent was evaporated
customto give the crude oily product, which
customwas purified by column chromatography (silica, 10% methanol: dichloromethane)

Sources & evidence

ORD record: ord-868a4287ec894ad8a8a4bf6d592a44da
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030150B2

Reaction notes

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