p-Toluenesulfonic acid → HCID 178419326, compound

HRID 1512184Notes

Reaction equation

HRID 1512184 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 (as prepared in STEP B above, 32.5 mmol) in toluene (5 ml). The resulting solution was stirred at 40° C. for 6 h. To the resulting solution was added p-toluenesulfonic acid (3.0 g, 16 mmol) and heated to reflux for 18 h. The resulting solution was concentrated. The residue obtained was partitioned between ethyl acetate and a saturated solution of sodium bicarbonate. The layers were separated. The organic layer was washed successively with saturated sodium bicarbonate, water, brine, then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed using a silica gel to yield 5-bromo-2-(2-cyclohexyl-vinyl)-1H-benzoimidazole.

Workup

  1. customas prepared in STEP B above
  2. temperatureheated
  3. temperatureto reflux for 18 h
  4. concentrationThe resulting solution was concentrated
  5. customThe residue obtained
  6. customwas partitioned between ethyl acetate
  7. customThe layers were separated
  8. washThe organic layer was washed successively with saturated sodium bicarbonate, water, brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was chromatographed

Sources & evidence

ORD record
ord-ff8b38192070449aae6768c8b99ed31b
Source dataset
uspto-grants-2012_07
Patent number
US08217060B2

Reaction notes

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