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

HRID 66761

Reaction equation

HRID 66761 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-52e50704029f482f85e1790684a02ab5
Source dataset
uspto-grants-1982_08
Patent number
US04343810

Linked notes

Loading…