Ethanolamine → 2-chloro-5-beta-aminoethylamino-4-nitro-N-(beta-hydroxyethyl)aniline

HRID 4239Notes

Reaction equation

HRID 4239 reaction equation
[Cl:1][C:2]1[C:11](Cl)=[CH:10][C:5]([NH:6][CH2:7][CH2:8][NH2:9])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1.[CH2:16]([CH2:18][NH2:19])[OH:17]>O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([NH:6][CH2:7][CH2:8][NH2:9])=[CH:10][C:11]=1[NH:19][CH2:18][CH2:16][OH:17]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 54360568N-(4,5-dichloro-2-nitrophenyl)ethane-1,2-diamine

Product 1

HCID 541600842-chloro-5-beta-aminoethylamino-4-nitro-N-(beta-hydroxyethyl)aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.04 mole (10 g) of 4,5-dichloro-2-nitro-N-β-aminoethylaniline prepared in the 1st stage is heated in 40 ml of monoethanolamine for 30 minutes to 100° C. The reaction mixture is diluted with 450 ml of iced water. An impurity is precipitated by adding hydrochloric acid and is removed by filtration. The filtrate is made alkaline with concentrated sodium hydroxide solution. The expected product precipitates. After filtration and drying, it is purified as its hydrochloride before being recrystallized from alcohol. It melts at 160° C.

Workup

  1. customAn impurity is precipitated
  2. additionby adding hydrochloric acid
  3. customis removed by filtration
  4. customThe expected product precipitates
  5. filtrationAfter filtration
  6. customdrying
  7. customit is purified as its hydrochloride
  8. custombefore being recrystallized from alcohol

Sources & evidence

ORD record
ord-4c54e3751d4842d7a5094d5ea6aa2e59
Source dataset
uspto-grants-1988_02
Patent number
US04725283

Reaction notes

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