Water → HCID 22120967, compound

HRID 1274369Notes

Reaction equation

HRID 1274369 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].Br[CH2:13][CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:13][CH2:14][CH2:15][N:16]2[C:20](=[O:21])[C:19]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]3[C:17]2=[O:26])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 691274-Chloro-3-nitrophenol

Product 1

HCID 22120967HCID 22120967, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-chloro-3-nitrophenol (5.00 g, 29 mmol) in N,N-dimethylformamide (100 ml) were added N-(3-bromopropyl)phthalimide (9.27 g, 35 mmol) and potassium carbonate (4.93 g, 36 mmol), followed by stirring at 60° C. for 6 hours. After allowing to stand overnight, the reaction solution was poured into water, and the insoluble matter was collected by filtration and washed with ethyl acetate and dried under reduced pressure to give N-[3-(4-chloro-3-nitrophenoxy)-propyl]phthalimide (7.78 g).

Workup

  1. waitto stand overnight
  2. filtrationthe insoluble matter was collected by filtration
  3. washwashed with ethyl acetate
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-7bf521f0f10e4947a5cdace9966da007
Source dataset
uspto-grants-2000_12
Patent number
US06156801

Reaction notes

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