Dimethylformamide → 2-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione

HRID 918590Notes

Reaction equation

HRID 918590 reaction equation
Br[CH:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[OH:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].C(N(CC)CC)C.CN(C)C=O>O>[CH:2]1([O:7][N:8]2[C:9](=[O:18])[C:10]3=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]3[C:12]2=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8728BromocyclopentaneHCID 10665N-Hydroxyphthalimide

Product 1

HCID 102632872-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dioneYield 49.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of bromocyclopentane (14.9 g), N-hydroxyphthalimide (16.3 g), triethylamine (15 ml), and dimethylformamide (30 ml) was stirred for 16 hours, then poured into water (500 ml). The oily mixture was extracted with ethyl acetate, and the combined extracts, after washing (water), drying, and removal of solvent gave a white solid. This solid was recrystallised from ethanol to give N-cyclopentyloxyphthalimide (11.37 g, 49%); m.p. 81.2°-82.5°; νmax. (CHBr3) include 1780, 1720 cm-1 (CO-N-CO), 970 cm-1 ##EQU20## τ values (DMSO--d6) 2.08 (4 Ar--H), 5.12 (cyclopentyl 1--H), 8.18 (4-CH2).

Workup

  1. extractionThe oily mixture was extracted with ethyl acetate
  2. washthe combined extracts, after washing (water)
  3. customdrying
  4. customremoval of solvent
  5. customgave a white solid
  6. customThis solid was recrystallised from ethanol

Sources & evidence

ORD record
ord-93ba518788614a53bd0820e9c6e6a0a6
Source dataset
uspto-grants-1976_07
Patent number
US03971778

Reaction notes

Loading…