p-Toluenesulfonic acid → HCID 15018890, compound

HRID 344588Notes

Reaction equation

HRID 344588 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[C:13]3[CH2:16][CH2:17][CH2:18][CH2:19][C:12]=3[C:11]2=[O:20])=[CH:6][C:5]=1[OH:21])[CH:2]=[CH2:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C(C)=CC=CC=1>[CH3:3][CH:2]1[CH2:1][C:4]2[CH:9]=[CH:8][C:7]([N:10]3[C:11](=[O:20])[C:12]4[CH2:19][CH2:18][CH2:17][CH2:16][C:13]=4[C:14]3=[O:15])=[CH:6][C:5]=2[O:21]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 15018888HCID 15018888, compound

Product 1

HCID 15018890HCID 15018890, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 0.20 g of 1C, 100 mg of p-toluenesulfonic acid (PTSA), and 10 mL of xylene was refluxed for 24 hours, then cooled and poured into a saturated aqueous solution of sodium bicarbonate. The resulting mixture was extracted with ethyl acetate, and the extract was washed in succession with sodium bicarbonate solution, water and brine, dried (Na2SO4) and filtered. The solvent was evaporated and the residue was chromatographed on a Chromatotron™ plate, starting with a 3:17 v:v mixture of ethyl acetate and hexane as eluent and gradually increasing the ethyl acetate content in the eluent, to give the title compound, as yellow crystals, m.p.: 114°-118° C.

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperaturecooled
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washthe extract was washed in succession with sodium bicarbonate solution, water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe solvent was evaporated
  8. customthe residue was chromatographed on a Chromatotron™ plate
  9. additionv mixture of ethyl acetate and hexane as eluent
  10. temperaturegradually increasing the ethyl acetate content in the eluent

Sources & evidence

ORD record
ord-a9cb3a1ce08b4cadb9cb927aa7462ba4
Source dataset
uspto-grants-1991_10
Patent number
US05053071

Reaction notes

Loading…