Ethylenediamine → HCID 67922840, compound

HRID 980422Notes

Reaction equation

HRID 980422 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH2:12]([NH2:15])[CH2:13][NH2:14]>Cl>[ClH:1].[NH2:14][CH2:13][CH2:12][NH:15][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 102833-Chloro-4-nitrophenol

Product 1

HCID 67922840HCID 67922840, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
-10 °C

Procedure

0.432 mol (75 g) of 3-chloro-4-nitrophenol is introduced into 282 ml of ethylenediamine and the reaction mixture is heated on a boiling waterbath for 13 hours. The cooled solution is then poured into 2.6 liters of ice-water to which 1.09 liters of hydrochloric acid (d=1.18) have been added. After the mixture has been cooled to -10° C. for a few hours, 3-β-aminoethylamino-4-nitrophenol hydrochloride crystallises. It is filtered off with suction and washed with an ice-cold 2N hydrochloric acid solution and then with ethanol. After recrystallisation from water, the dried product melts, with decomposition, at a temperature above 260° C.

Workup

  1. temperaturethe reaction mixture is heated on a boiling waterbath for 13 hours
  2. additionhave been added
  3. custom3-β-aminoethylamino-4-nitrophenol hydrochloride crystallises
  4. filtrationIt is filtered off with suction
  5. washwashed with an ice-cold 2N hydrochloric acid solution
  6. customAfter recrystallisation from water
  7. customat a temperature above 260° C.

Sources & evidence

ORD record
ord-e09cfcb9ea4d405285907d23d5e3299d
Source dataset
uspto-grants-1987_01
Patent number
US04637821

Reaction notes

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