p-Toluenesulfonic acid → HCID 24901650, compound

HRID 1685640Notes

Reaction equation

HRID 1685640 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=2)O)[CH:5]=[CH:6][CH:7]=1.[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=2)[N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 92571H-1,2,4-TriazoleHCID 58734007HCID 58734007, compound

Product 1

HCID 24901650HCID 24901650, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Bis-(3-hydroxyphenyl)methanol (0.75 g, 3.47 mmol), 1,2,4-triazole (0.48 g, 6.94 mmol), p-TSA (125 mg) and toluene (300 mL) were dissolved/suspended in toluene and heated at reflux with a Dean-Stark separator for 24 h. The reaction mixture was allowed to cool, and the solvent was removed in vacuo. The resulting residue was dissolved in EtOAc (75 mL) and the organic layer was washed with H2O (3×75 mL), dried (MgSO4) and the solvent was removed in vacuo to give a brown solid. The crude product was purified by flash column chromatography (EtOAc:Hexane 3:1) to give the title compound (0.82 g, 88%) as a pale yellow oil which formed a foam after a prolonged period under high vacuum; δH (270 MHz, d6-DMSO) 9.50 (2H, br s, ArOH), 8.55 (1H, s, NCHN), 8.06 (1H, s, NCHN), 7.16 (2H, t, J=7.9, ArH), 6.89 (1H, s, CH), 6.75-6.68 (2H, m, ArH), 6.67-6.60 (4H, m, ArH); δC (100 MHz, d6-DMSO) 158.0 (2×C), 152.3 (CH), 144.9 (CH), 141.0 (2×C), 130.2 (2×CH), 119.3 (2×CH), 115.6 (2×CH), 115.6 (2×CH), 66.2 (CH); LRMS (FAB+) 268.3 ([M+H]+, 100%), 199.2 (85); HRMS (FAB+) Found 268.1091, C15H14N3O2 requires 268.1086; HPLC (CH3CN/H2O, 90:10) tR=1.79 min (purity: 99+%).

Workup

  1. temperatureheated
  2. temperatureat reflux with a Dean-Stark separator for 24 h
  3. temperatureto cool
  4. customthe solvent was removed in vacuo
  5. dissolutionThe resulting residue was dissolved in EtOAc (75 mL)
  6. washthe organic layer was washed with H2O (3×75 mL)
  7. dry with materialdried (MgSO4)
  8. customthe solvent was removed in vacuo
  9. customto give a brown solid
  10. customThe crude product was purified by flash column chromatography (EtOAc:Hexane 3:1)

Sources & evidence

ORD record
ord-4fea65af909849d6af8df63032ae9e46
Source dataset
uspto-grants-2012_04
Patent number
US08148415B2

Reaction notes

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