Methanol → HCID 178497357, compound

HRID 1796340Notes

Reaction equation

HRID 1796340 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

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 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

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

Sources & evidence

ORD record
ord-868a4287ec894ad8a8a4bf6d592a44da
Source dataset
uspto-grants-2006_04
Patent number
US07030150B2

Reaction notes

Loading…