HCID 178488956, compound → HCID 178488955, compound

HRID 275791

Reaction equation

HRID 275791 reaction equation
[OH:1][CH:2]([C:4]1[NH:5][C:6]2[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1)[CH3:3]>C(O)(=O)C.O.[O-2].[O-2].[O-2].[Cr+6]>[C:2]([C:4]1[NH:5][C:6]2[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1)(=[O:1])[CH3:3]

Participants

5

Reactant 1

HCID 178488956HCID 178488956, compound

Product 1

HCID 178488955HCID 178488955, compoundYield 64.9%

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 2-(1-hydroxyethyl)-4-methoxybenzimidazole (2.18 g) in acetic acid (8.5 ml) was heated at 100° C. and treated with a solution of chromium trioxide (0.85 g) in water (3 ml). After 10 minutes the reaction was poured into water (110 ml), the precipitate was removed by filtration through a plug of Celite and the product extracted with dichloromethane (3×100 ml). The combined organic layers were dried over magnesium sulphate, filtered, and evaporated in vacuo and to yield the desired product as a light-brown solid (1.4 g).

Workup

  1. customthe precipitate was removed by filtration through a plug of Celite
  2. extractionthe product extracted with dichloromethane (3×100 ml)
  3. dry with materialThe combined organic layers were dried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-50946e4324434e8ab05bfeec541f53ca
Source dataset
uspto-grants-2002_03
Patent number
US06353010B1

Linked notes

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