Epichlorohydrin → 1-(2'-Acetylamino-5'-nitrophenoxy)-2,3-epoxypropane

HRID 477380Notes

Reaction equation

HRID 477380 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[OH:14])(=[O:3])[CH3:2].[CH2:15]([CH:17]1[O:19][CH2:18]1)Cl>[OH-].[Na+]>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[O:14][CH2:15][CH:17]1[O:19][CH2:18]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 3749260N-(2-Hydroxy-4-nitrophenyl)acetamide

Product 1

HCID 198355151-(2'-Acetylamino-5'-nitrophenoxy)-2,3-epoxypropane

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

0.376 mol (73.7 g) of 2-acetylamino-5-nitrophenol is dissolved in 375 ml of 1.1 N sodium hydroxide solution, and 300 ml of epichlorohydrin are then added. The reaction medium is left to stand for 96 hours at 20° C., with thorough stirring, and the expected product which has precipitated is then filtered off and washed with water. After recrystallisation from ethanol and drying in vacuo, it melts at 164° C.

Workup

  1. waitThe reaction medium is left
  2. customthe expected product which has precipitated
  3. filtrationis then filtered off
  4. washwashed with water
  5. customAfter recrystallisation from ethanol
  6. customdrying in vacuo, it melts at 164° C.

Sources & evidence

ORD record
ord-0ca5e0ad5394429dbf5cd0e14cd6146e
Source dataset
uspto-grants-1989_12
Patent number
US04888025

Reaction notes

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