Water → 1-Amino-5-fluoro-4-(2-hydroxyethylamino)-2-nitrobenzene

HRID 974146Notes

Reaction equation

HRID 974146 reaction equation
[CH2:1]1[O:3][CH2:2]1.[NH2:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([NH2:12])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14].O>COCCOC>[NH2:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([NH:12][CH2:2][CH2:1][OH:3])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 6354Ethylene OxideHCID 54884551,4-Benzenediamine, 2-fluoro-5-nitro-

Product 1

HCID 148170831-Amino-5-fluoro-4-(2-hydroxyethylamino)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Ethylene oxide is passed in portions into a mixture of 34 g (0.2 mol) of 1,4-diamino-5-fluoro-2-nitrobenzene, 200 ml of water and 17 g of monoethylene glycol dimethyl ether at 60° C. in the course of 90 minutes and the reaction is monitored by thin layer chromatography. When the monohydroxyethylation is complete, the mixture is cooled slowly to room temperature and the solid precipitate is filtered off and washed twice with 25 ml of a water/ethanol mixture (1/1) each time.

Workup

  1. filtrationthe solid precipitate is filtered off
  2. washwashed twice with 25 ml of a water/ethanol mixture (1/1) each time

Sources & evidence

ORD record
ord-c63f2adb295540c98064f19a2a24daac
Source dataset
uspto-grants-1991_11
Patent number
US05067967

Reaction notes

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