1,2-Dichlorobenzene → 2-((2,4-Dichloroanilino)methyl)-2-imidazoline p-toluenesulfonate

HRID 66761

反応式

HRID 66761 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[NH:4][CH2:5][C:6]#[N:7].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1.[CH2:24](N)[CH2:25][NH2:26].ClC1C=CC=CC=1Cl>C(Cl)Cl>[C:13]1([CH3:23])[CH:14]=[CH:15][C:16]([S:19]([OH:22])(=[O:20])=[O:21])=[CH:17][CH:18]=1.[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[NH:4][CH2:5][C:6]1[NH:26][CH2:25][CH2:24][N:7]=1

参加物

5

反応物 3

HCID 72391,2-DichlorobenzeneHCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 12832563(2,4-Dichloroanilino)acetonitrile

生成物 1

HCID 205290662-((2,4-Dichloroanilino)methyl)-2-imidazoline p-toluenesulfonate収率 84.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 21.5 grams (g) of 2,4-dichloroanilinoacetonitrile, 23.3 g of ethylenediamine p-toluenesulfonate and 75 milliliters (ml) of 1,2-dichlorobenzene was heated with stirring in a round-bottomed three-necked flask at from about 140°-170° C. for about 70 minutes under a small flow of nitrogen. The reaction mixture was cooled and then diluted with methylene chloride. The mixture was cooled and then filtered, which gave 35.1 g of 2-((2,4-dichloroanilino)methyl)-2-imidazoline p-toluenesulfonate as white crystals. The p-toluenesulfonate salt was slurried in water and CH2Cl2 and then basified. The CH2Cl2 layer was separated and the remaining aqueous portion extracted with CH2Cl2 and then CHCl3. The extracts were combined, treated with diatomaceous earth and activated charcoal, and then filtered. Concentrating the filtrate to dryness, left 17.0 g of crystals. Recrystallization from ethylene dichloride gave 14.0 g of purified 2-((2,4-dichloroanilino)methyl)-2-imidazoline as white crystals, having a melting point (m.p.) of 154°-156° C.

後処理

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. temperatureThe mixture was cooled
  4. filtrationfiltered

出典と根拠

ORDレコード
ord-52e50704029f482f85e1790684a02ab5
出典データセット
uspto-grants-1982_08
特許番号
US04343810

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