p-Toluenesulfonic acid → HCID 12150663, compound

HRID 2086146Notes

Reaction equation

HRID 2086146 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=C[CH:2]=1.C(OC(=O)C(=N[NH:19][C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([O:27][C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH:35]([CH3:37])[CH3:36])[CH:29]=2)=[C:22]([CH3:38])[CH:21]=1)C)C.[C:40]([O-:43])(O)=[O:41].[Na+].[C:45](OCC)(=O)[CH3:46]>C1(C)C=CC=CC=1>[CH2:45]([O:43][C:40]([C:1]1[NH:19][C:20]2[C:21]([CH:2]=1)=[C:22]([CH3:38])[C:23]([O:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([CH:35]([CH3:37])[CH3:36])[CH:29]=1)=[C:24]([CH3:26])[CH:25]=2)=[O:41])[CH3:46]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86587764HCID 86587764, compound

Product 1

HCID 12150663HCID 12150663, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of p-toluenesulfonic acid (130 mg, 0.75 mmol) and 2-{[4-(4-hydroxy-3-isopropyl-phenoxy)-3,5-dimethyl-phenyl]-hydrazono}-propionic acid ethyl ester (193 mg, 0.50 mmol) in toluene (2 mL) was heated to reflux for 2 hours and then cooled to room temperature. Saturated aqueous NaHCO3 (10 mL) and ehtyl acetate (25 mL) were added. The organic layer was separated, washed with saturated NaHCO3 (2 times 25 mL), 1M hydrochloric acid (25 mL), brine (25 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified by preparative thin layer chromatography (3% methanol in methylene chloride ) to afford the title compound (60 mg) as a solid. 1H NMR (400 MHz, CDCl3) δ8.82 (s, 1H), 7.20 (s, 1H), 7.09 (s, 1H), 6.74 (d, 1H), 6.55 (d, 1H), 6.28-6.25 (m, 1H), 4.41-4.35 (q, 2H), 3.15-3.11 (m, 1H), 2.30 (s, 3H), 2.20 (s, 3H), 1.40 (t, 3H), 1.18 (d, 6H). MS (APCI−) Calc: 367.2, Found: 366.3 (M−1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customThe organic layer was separated
  4. washwashed with saturated NaHCO3 (2 times 25 mL), 1M hydrochloric acid (25 mL), brine (25 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by preparative thin layer chromatography (3% methanol in methylene chloride )

Sources & evidence

ORD record
ord-5624f70848464bd7a79a618a0a8059a8
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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