Water → HCID 20528507, compound

HRID 67089Notes

Reaction equation

HRID 67089 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([S:9][CH2:10][C:11]#[N:12])[CH:6]=[CH:5][C:3]=1[NH2:4].[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.O>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.[NH2:4][C:3]1[CH:5]=[CH:6][C:7]([S:9][CH2:10][C:11]2[NH:26][CH2:25][CH2:24][N:12]=2)=[CH:8][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 962WaterHCID 72391,2-Dichlorobenzene2×HCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 20528505HCID 20528505, compound

Product 1

HCID 20528507HCID 20528507, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound, 2-(((4-amino-3-chlorophenyl)-thio)methyl)-2-imidazoline p-toluenesulfonate was prepared by refluxing a mixture of 2-chloro-4-cyanomethylthioaniline (10 g), ethylenediamine p-toluenesulfonate (12 g) and 1,2-dichlorobenzene (150 ml). The reaction mixture was cooled and most of the 1,2-dichlorobenzene decanted off, leaving a viscous residue. Water and methylene chloride were added to the viscous residue and the mixture basified. The methylene chloride layer was separated and approximately 10 g of viscous residue obtained. The residue was dissolved in dimethoxyethane and 5 N hydrochloric acid in isopropanol added. Recrystallization from absolute ethanol containing HCl and then from dimethoxyethane gave 2-(((4-amino-3-chlorophenyl)thio)methyl)-2-imidazoline dihydrochloride, m.p. 195°-199° C.

Workup

  1. temperatureby refluxing
  2. customdecanted off
  3. customleaving a viscous residue
  4. customThe methylene chloride layer was separated

Sources & evidence

ORD record
ord-16b4e91e911644e4a4d7fe30fa65a7b6
Source dataset
uspto-grants-1982_08
Patent number
US04344958

Reaction notes

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