Ethylenediamine → 4-Chloro-2-(beta-aminoethyl)amino-6-(beta-aminoethyl)aminonitrobenzene

HRID 231376Notes

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].[CH2:13]([NH2:16])[CH2:14][NH2:15]>O1CCOCC1>[Cl:8][C:6]1[CH:5]=[C:4]([NH:15][CH2:14][CH2:13][NH2:16])[C:3]([N+:10]([O-:12])=[O:11])=[C:2]([NH:15][CH2:14][CH2:13][NH2:16])[CH:7]=1

Participants

Conditions

Temperature: 10 °C

Procedure

0.35 mole (79 g) of 2,4,6-trichloronitrobenzene is added to 280 ml of ethylenediamine diluted with 140 ml of dioxan, the temperature being maintained at 10° C. The mixture is heated for 2 hours at 50° C. The product expected precipitates on standing overnight at ambient temperature. After draining and re-impasting in water, the product is recrystallized from isopropanol in order to remove an insoluble product by filtering in the heated state. After drying under reduced pressure in the presence of phosphorous pentoxide, it melts at 113° C.

Workup

temperatureThe mixture is heated for 2 hours at 50° C
customThe product expected precipitates
customthe product is recrystallized from isopropanol in order
customto remove an insoluble product
filtrationby filtering in the heated state
dry with materialAfter drying under reduced pressure in the presence of phosphorous pentoxide, it melts at 113° C.

Sources & evidence

ORD record: ord-7fe7cdb41be94795b36ccba555bb7f17
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04845293

Reaction notes

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