Water → HCID 69135061, compound

HRID 969515Notes

Reaction equation

HRID 969515 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:13]C(C2C=CC=CC=2)C=C)[C:5]2[N:9]=[C:8]([CH3:10])[N:7]([CH3:11])[C:6]=2[CH:12]=1.O.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27](S(O)(=O)=O)=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+].O.[C:41]1(C)C=CC=C[CH:42]=1>>[Br:1][C:2]1[C:3]([CH2:41][CH:42]=[CH:34][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:4]([NH2:13])[C:5]2[N:9]=[C:8]([CH3:10])[N:7]([CH3:11])[C:6]=2[CH:12]=1

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 69135079HCID 69135079, compound

Product 1

HCID 69135061HCID 69135061, compoundYield 64%

Procedure

A suspension of 3.8 g (10.7 mmol) (6-bromo-1,2-dimethyl-1H-benzimidazol-4-yl)-(1-phenyl-allyl)-amine and 3.5 g p-toluenesulphonic acid monohydrate in 80 ml toluene was refluxed for 26 h. The suspension was poured into a mixture of 50 ml saturated sodium hydrogencarbonate solution and 150 ml water and extracted with ethyl acetate. The organic phase was separated, dried over anhydrous magnesium sulfphate and evaporated. The residue was purified by column chromatography on silica gel (toluene/dioxane/methanol=6:3.8:0.2). Crystallization from diisopropyl ether gave 2.45 g (64%) of the title compound as a colourless solid. m.p. 186-189° C.

Workup

  1. temperaturewas refluxed for 26 h
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous magnesium sulfphate
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (toluene/dioxane/methanol=6:3.8:0.2)
  7. customCrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-ddd0835610034fe9853a1159313a18d1
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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