Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → p-Toluenesulfonic acid

HRID 1854519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1854519
NN1C(C)=NN=N1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([O-:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1.[NH+]1C=CC=CC=1>C(O)C>[CH3:18][C:8]1[CH:9]=[CH:10][C:11]([S:14]([OH:17])(=[O:16])=[O:15])=[CH:12][CH:13]=1

Komponenten

4

Edukt 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 40764305-Methyl-1-aminotetrazole

Produkt 1

HCID 6101p-Toluenesulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

2,2′-[[3-[N-(3-Hydroxypropyl)-N-methylamino]phenyl]methylene]bis[4-[[(5-methyl-1H-tetrazol-1-yl)imino]methyl]]phenol. 1-Amino-5-methyltetrazole (71 mg, 0.72 mmol) and pyridinium para-toluenesulfonate (6 mg, 0.024 mmol) were dissolved in absolute ethanol (10 ml) and heated to reflux for 15 minutes. Compound 37(f) (0.17 g, 0.41 mmol) in ethanol (6 ml) was added dropwise to the solution. The reaction was stirred at reflux for 3 hours, and then cooled to room temperature overnight. The solvent was removed in vacuo and diluted with t-butyl methyl ether to provide the tosic acid salt, which was isolated by filtration and dried in vacuo. This solid was treated with sodium bicarbonate (20 mg) in water (6 to 7 ml) and ethyl acetate to form the free base. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organics were dried over MgSO4, filtered, and concentrated by rotary evaporation to provide 0.12 g of the desired product.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 15 minutes
  3. temperatureat reflux for 3 hours
  4. customThe solvent was removed in vacuo
  5. additiondiluted with t-butyl methyl ether

Quellen und Nachweise

ORD-Eintrag
ord-7ac79684bf494d2aba7fb2f84c834785
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962667B2

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