2-Methoxyethylamine → 3,5-Dinitro-4-[2-methoxyethyl-amino]-2-chlorobenzotrifluoride

HRID 1577105Notes

Reaction equation

HRID 1577105 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[Cl:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[C:11](Cl)[C:10]([N+:17]([O-:19])=[O:18])=[CH:9][C:8]=1[C:20]([F:23])([F:22])[F:21]>C(Cl)(Cl)Cl>[N+:13]([C:12]1[C:7]([Cl:6])=[C:8]([C:20]([F:21])([F:22])[F:23])[CH:9]=[C:10]([N+:17]([O-:19])=[O:18])[C:11]=1[NH:5][CH2:4][CH2:3][O:2][CH3:1])([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 943982,4-Dichloro-1,3-dinitro-5-(trifluoromethyl)benzene

Product 1

HCID 205718683,5-Dinitro-4-[2-methoxyethyl-amino]-2-chlorobenzotrifluoride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 9.8 g (0.131 mole) of 2-methoxyethylamine in 20 ml of chloroform is added dropwise at 0°-5° C. to a solution of 20 g (0.065 mole) of 2,4-dichloro-3,5-dinitro-benzotrifluoride in 40 ml of chloroform. The reaction mixture is stirred for 2 hours at 0°-5° C. and then for 18 hours at room temperature. For working up, the reaction mixture is concentrated and the residue is taken up in ether. The ethereal solution is washed twice with water and three times with sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue is recrystallised from isopropanol, affording 3,5-dinitro-4-[2-methoxyethyl-amino]-2-chlorobenzotrifluoride with a melting point of 104°-105° C.

Workup

  1. waitfor 18 hours at room temperature
  2. concentrationthe reaction mixture is concentrated
  3. washThe ethereal solution is washed twice with water and three times with sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is recrystallised from isopropanol

Sources & evidence

ORD record
ord-68edcdd5197c4718965b2a6de6f0aad3
Source dataset
uspto-grants-1981_09
Patent number
US04287204

Reaction notes

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