Epichlorohydrin → 4-Glycidoxy-2-nitroacetanilide

HRID 477378Notes

Reaction equation

HRID 477378 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[N+:6]([C:9]1[CH:10]=[C:11]([OH:19])[CH:12]=[CH:13][C:14]=1[NH:15][C:16](=[O:18])[CH3:17])([O-:8])=[O:7]>[OH-].[Na+]>[N+:6]([C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][C:14]=1[NH:15][C:16](=[O:18])[CH3:17])[O:19][CH2:1][CH:3]1[O:5][CH2:4]1)([O-:8])=[O:7]

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 4024832N-(4-hydroxy-2-nitrophenyl)acetamide

Product 1

HCID 3597004-Glycidoxy-2-nitroacetanilide

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

150 ml of epichlorohydrin are added, at ambient temperature, to a solution of 0.376 mol (73.7 g) of 3-nitro-4-acetylaminophenol in 375 ml of 1.1N sodium hydroxide solution. The reaction medium is left to stand at ambient temperature for 48 hours, with thorough stirring, and the expected product which has precipitated is then filtered off. After drying in vacuo and recrystallisation from benzene, this product melts at 123° C.

Workup

  1. waitThe reaction medium is left
  2. customthe expected product which has precipitated
  3. filtrationis then filtered off
  4. dry with materialAfter drying in vacuo and recrystallisation from benzene

Sources & evidence

ORD record
ord-6d1a094025774fb68477135b6ab6ba48
Source dataset
uspto-grants-1989_12
Patent number
US04888025

Reaction notes

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