p-Toluenesulfonic acid → HCID 10686987, compound

HRID 1585062Notes

Reaction equation

HRID 1585062 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][CH2:13][C:14](=O)[CH3:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH:18]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:18]1([N:24]2[C:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)=[CH:12][CH:13]=[C:14]2[CH3:15])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7965CyclohexylamineHCID 105388711-[4-(Methylsulfonyl)phenyl]-1,4-pentanedione

Product 1

HCID 10686987HCID 10686987, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(4-methylsulfonylphenyl)-1,4-pentanedione (Example 1, Step 2) (820 mg, 3.23 mmol), cyclohexylamine (410>1, 3.55 mmol) and p-toluenesulfonic acid (50 mg) in toluene (75 ml) was heated to reflux for 24 hours. The reaction mixture was cooled, filtered and concentrated. The crude solid (1.14 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 1/1) to give 1-cyclohexyl-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole (350 mg, p6%) as a white solid: mp (DSC) 141 ° C. Anal Calc'd. for C18H23NSO2 : C, 68.10; H, 7.30; N, 4.41; S, 10.10. Found: C, 68.22; H, 7.25; N, 4.30; S, 10.16.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude solid (1.14 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 1/1)

Sources & evidence

ORD record
ord-51aaebf162c4492d87f6cfbbc5262109
Source dataset
uspto-grants-1999_08
Patent number
US05935990

Reaction notes

Loading…