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

HRID 1606861Notes

Reaction equation

HRID 1606861 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-propanediol

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 of 0.1 mole (22.6 g) of 2,4,6-trichloro nitrobenzene and 54.7 g of 3-amino-1,2-propanediol in 20 ml of dioxan was refluxed for 4 hours followed by evaporation of the dioxan under reduced pressure. The oil obtained was diluted in about 300 ml of water. The desired product was obtained using HPLC in two stages. About 200 ml of the aqueous solution of the product containing 3-amino-1,2-propanediol were injected onto a C18RD chromatographic column (Instrument: Waters Prep 500). The desired product was eluted using 35% methanol-65% water solution. After evaporation of the fractions containing the desired product, a dry extract was obtained which was recrystallized from 96° alcohol. The product melted at 146° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customfollowed by evaporation of the dioxan under reduced pressure
  3. customThe oil obtained

Sources & evidence

ORD record
ord-b2fe27185eb74be799f546339359a609
Source dataset
uspto-grants-1989_09
Patent number
US04863482

Reaction notes

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