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

HRID 2037234노트

반응식

HRID 2037234 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 6101p-Toluenesulfonic acid

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-44484e38412f4df98cdd92ee1b9d5e79
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575205B2

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