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2-Methoxyethylamine → 4-Chloro-2-(beta-methoxyethyl)amino-6-(beta-methoxyethyl)aminonitrobenzene

HRID 2291444
Notes
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Reaction equation

HRID 2291444 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][O:14][CH2:15][CH2:16][NH2:17]>O>[Cl:8][C:6]1[CH:5]=[C:4]([NH:17][CH2:16][CH2:15][O:14][CH3:13])[C:3]([N+:10]([O-:12])=[O:11])=[C:2]([NH:17][CH2:16][CH2:15][O:14][CH3:13])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 292282,4,6-Trichloronitrobenzene

Product 1

HCID 200710824-Chloro-2-(beta-methoxyethyl)amino-6-(beta-methoxyethyl)aminonitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

0.2 mole (45.3 g) of 2,4,6-trichloronitrobenzene is added portionwise, with stirring, to 180 ml of 2-methoxyethylamine, heated to 80° C. After the end of the addition the heating is continued for 2 hours 30 minutes. The reaction mixture is diluted with 180 ml of iced water. The expected product precipitates. It is filtered off, washed with water and dried under vacuum at 60° C. in the presence of phosphorus pentoxide. Recrystallized from 96° ethanol, it melts at 90° C.

Workup

  1. additionAfter the end of the addition the heating
  2. customThe expected product precipitates
  3. filtrationIt is filtered off
  4. washwashed with water
  5. dry with materialdried under vacuum at 60° C. in the presence of phosphorus pentoxide
  6. customRecrystallized from 96° ethanol, it melts at 90° C.

Sources & evidence

ORD record
ord-8979251e52e24cb09bf428ade98e1ae1
Source dataset
uspto-grants-1989_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04797129

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes