1-Amino-2-propanol → 4-Chloro-2-(beta-hydroxypropyl)amino-6-(beta-hydroxypropyl)aminonitrobenzene

HRID 231380Notes

Reaction equation

HRID 231380 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].[NH2:13][CH2:14][CH:15]([OH:17])[CH3:16]>>[Cl:8][C:6]1[CH:5]=[C:4]([NH:13][CH2:14][CH:15]([OH:17])[CH3:16])[C:3]([N+:10]([O-:12])=[O:11])=[C:2]([NH:13][CH2:14][CH:15]([OH:17])[CH3:16])[CH:7]=1

Participants

3

Reactant 2

HCID 41-Amino-2-propanolHCID 292282,4,6-Trichloronitrobenzene

Product 1

HCID 200710924-Chloro-2-(beta-hydroxypropyl)amino-6-(beta-hydroxypropyl)aminonitrobenzene

Conditions

Temperature
80 °C

Procedure

0.2 mole (45.3 g) of 2,4,6-trichloronitrobenzene is added in small portions to 180 ml of 3-amino-2-propanol heated to 80° C., with stirring. The reaction is exothermic. After heating for 3 hours 30 minutes, the reaction mixture is poured into 180 ml of ice-cold water. The product expected precipitates. It is drained, washed to neutrality with water and then dried under vacuum in the presence of phosphorous pentoxide. After recrystallization from 96° ethanol, it melts at 170° C.

Workup

  1. temperatureAfter heating for 3 hours 30 minutes
  2. customThe product expected precipitates
  3. washwashed
  4. dry with materialdried under vacuum in the presence of phosphorous pentoxide
  5. customAfter recrystallization from 96° ethanol, it melts at 170° C.

Sources & evidence

ORD record
ord-ec2eeb9133d949ceafab37321cf212de
Source dataset
uspto-grants-1989_07
Patent number
US04845293

Reaction notes

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