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

HRID 220213ノート

反応式

HRID 220213 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 6101p-Toluenesulfonic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5bbf4b703c534a62950c221d03956258
出典データセット
uspto-grants-2012_06
特許番号
US08202896B2

反応ノート

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