HCID 178491329, compound → HCID 178491328, compound

HRID 2054494Notes

Reaction equation

HRID 2054494 reaction equation
[CH:1]1([C:4]2[NH:5][C:6]3[C:12]([CH2:13][OH:14])=[CH:11][CH:10]=[C:9]([O:15][CH3:16])[C:7]=3[N:8]=2)[CH2:3][CH2:2]1>C1(C)C=CC=CC=1.ClCCl.[O-2].[O-2].[Mn+4]>[CH:1]1([C:4]2[NH:5][C:6]3[C:12]([CH:13]=[O:14])=[CH:11][CH:10]=[C:9]([O:15][CH3:16])[C:7]=3[N:8]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 1

HCID 178491329HCID 178491329, compound

Product 1

HCID 178491328HCID 178491328, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

A stirred suspension of 2-cyclopropyl-7-methoxy-3H-benzimidazole-4-methanol [7.73 g, Reference Example 22(a)] in a mixture of toluene (250 ml) and dichloromethane (150 ml), at room temperature and under nitrogen, was treated portionwise with activated manganese dioxide (11 g). The resulting suspension was stirred under nitrogen at 85° C. for 3 hours. The suspension was allowed to cool slightly and was then filtered through hyflosupercel washing the filter pad six times with hot ethyl acetate (50 ml). The combined filtrate and washings were dried over magnesium sulphate and then evaporated to yield the title compound as a cream coloured powder (7.26 g).

Workup

  1. temperatureto cool slightly
  2. filtrationwas then filtered through hyflosupercel
  3. washwashing the filter pad six times with hot ethyl acetate (50 ml)
  4. dry with materialThe combined filtrate and washings were dried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-e01927511dc4408daaf61085c63940d3
Source dataset
uspto-grants-2008_02
Patent number
US07329675B2

Reaction notes

Loading…