2-(4-Chloro-2-butenyl)-1,3-isoindolinedione → N-[4-(1H-imidazol-1-yl)-2-butenyl]isoindole-1,3-(2H)-dione

HRID 1589198Notes

Reaction equation

HRID 1589198 reaction equation
Cl[CH2:2][CH:3]=[CH:4][CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16].[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.[Na]>CN(C)C=O>[N:17]1([CH2:2][CH:3]=[CH:4][CH2:5][N:6]2[C:14](=[O:15])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]2=[O:16])[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

4

Reactant 2

HCID 27342002-(4-Chloro-2-butenyl)-1,3-isoindolinedioneHCID 57373095Imidazole sodium

Product 1

HCID 54070864N-[4-(1H-imidazol-1-yl)-2-butenyl]isoindole-1,3-(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 23.5 g. of N-(4-chloro-2-butenyl)-isoindole-1,3(2H)-dione, 11.0 g. of sodium imidazol and 200 ml. of dimethyl formamide was heated on the steam bath for 18 hours and concentrated to remove the solvent; the residue was taken up in methylene chloride, washed with water, dried with magnesium sulfate and again concentrated. The residue was dissolved in hot ethylacetate and allowed to cool and N-[4-(1H-imidazol-1-yl)-2-butenyl]isoindole-1,3-(2H)-dione, m.p. 106°-108° C., was obtained.

Workup

  1. additionA mixture of 23.5 g
  2. concentrationconcentrated
  3. customto remove the solvent
  4. washwashed with water
  5. dry with materialdried with magnesium sulfate
  6. concentrationagain concentrated
  7. dissolutionThe residue was dissolved in hot ethylacetate
  8. temperatureto cool

Sources & evidence

ORD record
ord-e63a9383f152491e91c0f1906601e64f
Source dataset
uspto-grants-1986_02
Patent number
US04568687

Reaction notes

Loading…