N-Hydroxyphthalimide → HCID 54486942, compound

HRID 2395938Notes

Reaction equation

HRID 2395938 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].Br[CH2:14][CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1>CN1CCCC1=O>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([CH:16]=[CH:15][CH2:14][O:1][N:2]2[C:3](=[O:12])[C:4]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]3[C:6]2=[O:7])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 10665N-HydroxyphthalimideHCID 545198061-Bromo-4-(3-bromoprop-1-en-1-yl)benzene

Product 1

HCID 54486942HCID 54486942, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
20 °C

Procedure

18.5 g (0.11 mol) of N-hydroxyphthalimide and 31.4 g (0.11 mol) of 1-bromo-[3-(4-bromophenyl)]-prop-2-ene were added in succession to 350 ml of dry N-methylpyrrolidone, after which 12.1 g (0.12 mol) of triethylaminewere added dropwise at room temperature. The reaction mixture was stirred for four days at 20° C. and then poured onto 1.5 l of ice water, and the product was filtered off and washed with water and isopropanol. Yield: 86.8%; mp.: 161°-162° C.

Workup

  1. additionafter which 12.1 g (0.12 mol) of triethylaminewere added dropwise at room temperature
  2. filtrationthe product was filtered off
  3. washwashed with water and isopropanol

Sources & evidence

ORD record
ord-bf0729f6974a46f09722c6de08bd79b2
Source dataset
uspto-grants-1996_02
Patent number
US05491123

Reaction notes

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