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

HRID 2291444Notes

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

Participants

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

additionAfter the end of the addition the heating
customThe expected product precipitates
filtrationIt is filtered off
washwashed with water
dry with materialdried under vacuum at 60° C. in the presence of phosphorus pentoxide
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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