2,4,6-Trichloronitrobenzene → 4-Chloro-2-(beta,gamma-dihydroxypropyl)amino-6-(beta,gamma-dihydroxypropyl)aminonitrobenzene

HRID 231384Notes

Reaction equation

HRID 231384 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:18])[CH2:16][OH:17]>O1CCOCC1.O>[Cl:8][C:6]1[CH:5]=[C:4]([NH:13][CH2:14][CH:15]([OH:18])[CH2:16][OH:17])[C:3]([N+:10]([O-:12])=[O:11])=[C:2]([NH:13][CH2:14][CH:15]([OH:18])[CH2:16][OH:17])[CH:7]=1

Participants

5

Reactant 2

HCID 292282,4,6-TrichloronitrobenzeneHCID 735613-Amino-1,2-propanediol2×

Product 1

HCID 544072844-Chloro-2-(beta,gamma-dihydroxypropyl)amino-6-(beta,gamma-dihydroxypropyl)aminonitrobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture consisting of 0.1 mole (22.6 g) of 2,4,6-trichloronitrobenzene and 54.7 g of 3-aminopropane-1,2-diol in 20 ml of dioxan is heated under reflux. After heating for 4 hours, the dioxan is evaporated under reduced pressure. The oil obtained is diluted with approximately 300 ml of water. The product expected is obtained by chromatography under pressure in two operations. Approximately 200 ml of the aqueous solution of the product expected containing 3-aminopropane-1,2-diol are injected onto a C18RD chromatrography column (Waters Prep 500 apparatus). The product expected is eluted with a solution containing 35% methanol and 65% water. After evaporation of the fractions containing the product expected, a dry extract is obtained, which is recrystallized from 96° alcohol.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. temperatureAfter heating for 4 hours
  4. customthe dioxan is evaporated under reduced pressure
  5. customThe oil obtained
  6. customThe product expected is obtained by chromatography under pressure in two operations
  7. washThe product expected is eluted with a solution
  8. additioncontaining 35% methanol and 65% water
  9. customAfter evaporation of the fractions
  10. additioncontaining the product
  11. extractiona dry extract
  12. customis obtained
  13. customwhich is recrystallized from 96° alcohol

Sources & evidence

ORD record
ord-3c635e0c1e104b8bbc5409b572f4d4d9
Source dataset
uspto-grants-1989_07
Patent number
US04845293

Reaction notes

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