Ethanol → 1-(2'-Acetylamino-5'-nitrophenoxy)-3-succinimidopropan-2-ol

HRID 477381Notes

Reaction equation

HRID 477381 reaction equation
[C:1]([NH:4][C:5]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:6]=1[O:7][CH2:8][CH:9]1[O:11][CH2:10]1)(=[O:3])[CH3:2].C(O)C.[C:22]1(=[O:28])[NH:26][C:25](=[O:27])[CH2:24][CH2:23]1>N1C=CC=CC=1.O>[C:1]([NH:4][C:5]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:6]=1[O:7][CH2:8][CH:9]([OH:11])[CH2:10][N:26]1[C:22](=[O:28])[CH2:23][CH2:24][C:25]1=[O:27])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 11439SuccinimideHCID 198355151-(2'-Acetylamino-5'-nitrophenoxy)-2,3-epoxypropane

Product 1

HCID 198355141-(2'-Acetylamino-5'-nitrophenoxy)-3-succinimidopropan-2-ol

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 962WaterSolvent2×

Procedure

0.072 mol (18.2 g) of 1-(2'-acetylamino-5'-nitrophenoxy)-2,3-epoxypropane is introduced into 60 ml of absolute ethanol to which 6 drops of pyridine have been added. 0.087 mol (8.6 g) of succinimide is added and the mixture is then heated under reflux for 5 hours. After cooling, 150 ml of water are added and the alcohol is driven off in vacuo. The expected product, which is obtained initially in the form of a water-insoluble oil, crystallises slowly. It is filtered off and recrystallised from 96° strength alcohol. After drying, it melts at 157° C.

Workup

  1. additionhave been added
  2. temperaturethe mixture is then heated
  3. temperatureunder reflux for 5 hours
  4. temperatureAfter cooling

Sources & evidence

ORD record
ord-89434cde9b5e4dc689558b4db3be625a
Source dataset
uspto-grants-1989_12
Patent number
US04888025

Reaction notes

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