p-Toluenesulfonic acid → HCID 178419326, compound

HRID 1512156Notes

Reaction equation

HRID 1512156 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[CH:10]1([CH:16]=[CH:17][C:18](Cl)=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:18]([CH:17]=[CH:16][CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)=[N:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 3235934-Bromobenzene-1,2-diamineHCID 566232073-Cyclohexylprop-2-enoyl chloride

Product 1

HCID 178419326HCID 178419326, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 4-bromo-benzene-1,2-diamine (3.0 g, 16.1 mmol) in anhydrous toluene (50 mL) was added a solution of 3-cyclohexyl-acryloyl chloride (32.5 mmol) in toluene (5 mL). The resulting solution was stirred at 40° C. for 6 h and then treated with p-toluenesulfonic acid (3.0 g, 16.1 mmol). The resulting mixture was heated at reflux for 18 h. allowed to cool to room temperature and concentrated. The residue obtained was partitioned between ethyl acetate and a saturated solution of sodium bicarbonate in water. The layers were separated. The organic layer was washed successively with saturated. sodium bicarbonate, water and brine, then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed on silica with ethyl acetate/hexanes 3:7 to yield 5-bromo-2-(2-cyclohexyl-vinyl)-1H-benzimidazole.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 18 h.
  3. temperatureto cool to room temperature
  4. concentrationconcentrated
  5. customThe residue obtained
  6. customwas partitioned between ethyl acetate
  7. customThe layers were separated
  8. washThe organic layer was washed successively with saturated
  9. dry with materialsodium bicarbonate, water and brine, then dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was chromatographed on silica with ethyl acetate/hexanes 3:7

Sources & evidence

ORD record
ord-6f38b63f1e89471cb3383a67dfc9bf0a
Source dataset
uspto-grants-2012_07
Patent number
US08217060B2

Reaction notes

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