1,2-Ethanediamine, 4-methylbenzenesulfonate (1:?) → p-Toluenesulfonic acid

HRID 66768

反応式

HRID 66768 の反応式
CC1C=CC(SCC#N)=CC=1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([OH:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1.C(N)CN>ClC1C=CC=CC=1Cl.C(Cl)Cl>[CH3:22][C:12]1[CH:17]=[CH:16][C:15]([S:18]([OH:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1

参加物

5

反応物 2

HCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 27997712-[(4-Methylphenyl)thio]acetonitrile

生成物 1

HCID 6101p-Toluenesulfonic acid

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 72391,2-Dichlorobenzene溶媒

実験手順

A mixture of 27 g of 4-methylthiophenoxyacetonitrile and 35 g of ethylenediamine p-toluenesulfonate in 50 ml of 1,2-dichlorobenzene was heated at 158°-180° C. for about 45 minutes. The reaction mixture was cooled, diluted with CH2Cl2 and filtered to obtain the p-toluenesulfonate salt. After washing with CH2Cl2, the p-toluenesulfonate salt was slurried with water and then 40 ml of an aqueous 5 normal (N) sodium hydroxide solution added to the slurry. Extracting the mixture with CH2Cl2 and then evaporating the CH2Cl2 left 30 g of the free base. The free base was heated in cyclohexane/methylchloroform, the resulting mixture was then cooled and the solids removed by filtration. The free base was then dissolved in 150 ml of isopropanol and acidified with hydrochloric acid (HCl) in isopropanol to give the hydrochloride salt (31 g). The 2-((4-(methylthio)phenoxy)methyl)-2-imidazoline hydrochloride was found to have a m.p. of 190°-191° C.

後処理

  1. temperaturewas heated at 158°-180° C. for about 45 minutes
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered

出典と根拠

ORDレコード
ord-a440dca77bc945aeab5a44eccc4bab0c
出典データセット
uspto-grants-1982_08
特許番号
US04343808

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