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

HRID 1154341

Reaction equation

HRID 1154341 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 imidazole 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-f5ef5eafe588410697b3bd75a7663cdd
Source dataset
uspto-grants-1984_12
Patent number
US04489089

Linked notes

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