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

HRID 231381Notes

Reaction equation

HRID 231381 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][CH2:15][CH2:16][OH:17]>>[Cl:8][C:6]1[CH:5]=[C:4]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])[C:3]([N+:10]([O-:12])=[O:11])=[C:2]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])[CH:7]=1

Participants

3

Reactant 2

HCID 90863-Amino-1-propanolHCID 292282,4,6-Trichloronitrobenzene

Product 1

HCID 200710684-Chloro-2-(gamma-hydroxypropyl)amino-6-(gamma-hydroxypropyl)aminonitrobenzene

Conditions

Temperature
80 °C

Procedure

0.22 mole (50 g) of 2,4,6-trichloronitrobenzene is added in portions to 150 ml of 3-amino-1-propanol heated to 80° C., with stirring. Heating is continued for 1 hour 30 minutes after the addition is complete. The reaction medium is poured into 300 g of ice-cold water. An oil which crystallizes on adding concentrated hydrochloric acid is obtained. The precipitate of the expected product is drained, washed with a 2N solution of hydrochloric acid and then with water to neutrality. After drying at 40° C. in the presence of phosphorous pentoxide, it is recrystallized from 96° ethanol. It melts at 127° C.

Workup

  1. temperatureHeating
  2. additionafter the addition
  3. customAn oil which crystallizes
  4. additionon adding concentrated hydrochloric acid
  5. customis obtained

Sources & evidence

ORD record
ord-39b2b952fc31474cacdc9ad9d063d4a7
Source dataset
uspto-grants-1989_07
Patent number
US04845293

Reaction notes

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