2-(beta-Hydroxyethyl)amino-6-(beta-hydroxyethyl)amino-4-chloronitrobenzene → 2-(beta-Hydroxyethyl)amino-6-(beta-hydroxyethyl)amino-4-(beta-aminoethyl)aminonitrobenzene

HRID 1606858Notes

Reaction equation

HRID 1606858 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[C:9](Cl)[CH:8]=[C:7]([NH:12][CH2:13][CH2:14][OH:15])[C:6]=1[N+:16]([O-:18])=[O:17]>C(N)CN>[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[C:9]([NH:4][CH2:5][CH2:6][NH2:16])[CH:8]=[C:7]([NH:12][CH2:13][CH2:14][OH:15])[C:6]=1[N+:16]([O-:18])=[O:17]

Participants

3

Reactant 1

HCID 200710912-(beta-Hydroxyethyl)amino-6-(beta-hydroxyethyl)amino-4-chloronitrobenzene

Product 1

HCID 198511702-(beta-Hydroxyethyl)amino-6-(beta-hydroxyethyl)amino-4-(beta-aminoethyl)aminonitrobenzene

Reagents, catalysts & solvents 1

HCID 3301EthylenediamineSolvent

Procedure

0.13 mole (36.5 g) of 2-(β-hydroxyethyl)amino-6-(β-hydroxyethyl)amino-4-chloronitrobenzene, whose synthesis was described in stage 1 of example 2, was heated for 2 hours at 130° C. in 150 ml of ethylenediamine, then the reaction medium diluted with 450 ml of ice water to precipitate out the desired product. After filtering and water washing to neutrality, the product obtained was dried under vacuum in the presence of P2O5. It was recrystallized from 96° ethanol and melted at 220° C.

Workup

  1. customthe reaction
  2. customto precipitate out the desired product
  3. filtrationAfter filtering
  4. customwater washing to neutrality, the product obtained
  5. dry with materialwas dried under vacuum in the presence of P2O5
  6. customIt was recrystallized from 96° ethanol and melted at 220° C.

Sources & evidence

ORD record
ord-a1373ab1801340939b767731612b3c47
Source dataset
uspto-grants-1989_09
Patent number
US04863482

Reaction notes

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