p-Toluenesulfonic acid → HCID 12150685, compound

HRID 2086162Notes

Reaction equation

HRID 2086162 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.C(OC(=O)C(=N[NH:19][C:20]1[CH:25]=[C:24]([Cl:26])[C:23]([O:27][C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([S:35]([CH2:38][CH3:39])(=[O:37])=[O:36])[CH:29]=2)=[C:22]([Cl:40])[CH:21]=1)C)C.[C:42]([O:45][CH2:46][CH3:47])(=[O:44])[CH3:43]>C1(C)C=CC=CC=1>[CH2:46]([O:45][C:42]([C:43]1[NH:19][C:20]2[C:21]([CH:1]=1)=[C:22]([Cl:40])[C:23]([O:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([S:35]([CH2:38][CH3:39])(=[O:36])=[O:37])[CH:29]=1)=[C:24]([Cl:26])[CH:25]=2)=[O:44])[CH3:47]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 87968875HCID 87968875, compound

Product 1

HCID 12150685HCID 12150685, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of p-toluenesulfonic acid (169 mg, 0.98 mmol) and 2-{[3,5-Dichloro-4-(3-ethanesulfonyl-4-hydroxy-phenoxy)-phenyl]-hydrazono}-propionic acid ethyl ester (310 mg, 0.65 mmol) in toluene (2.5 mL) was heated to reflux for 16 hours and then cooled to room temperature. The reaction mixture was diluted with ethyl acetate (25 mL), washed with saturated NaHCO3 (3 times 10 mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative thin layer chromatography (4% methanol in methylene chloride) to afford the title compound (100 mg) as a tan solid. 1H NMR (400 MHz, CDCl3) δ10.7 (s, 1H), 7.42 (s, 1H), 7.18 (d, 1H), 7.04-6.98 (m, 2H), 6.88 (d, 1H), 4.36-4.30 (q, 2H), 3.20-3.05 (q, 2H), 1.34 (t, 3H), 1.18 (t, 3H). MS (APCI−) Calc: 457.0, Found: 456.1 (M−1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. washwashed with saturated NaHCO3 (3 times 10 mL), brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative thin layer chromatography (4% methanol in methylene chloride)

Sources & evidence

ORD record
ord-f0d727fe810e4303a1096c742f1f7b8c
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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