HCID 13618117, compound → Phthalimide

HRID 1589196Notes

Reaction equation

HRID 1589196 reaction equation
BrCC#CC[N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].N1C=CN=C1.[Na]>CN(C)C=O>[C:7]1(=[O:16])[C:8]2[C:9](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:11])[NH:6]1

Participants

4

Reactant 2

HCID 13618117HCID 13618117, compoundHCID 57373095Imidazole sodium

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 27.8 g. of N-(4-bromo-2-butynyl)phthalimide, 9.0 g. of sodium imidazole and 150 ml. of dimethylformamide is heated at 80° C. for 3 hours and then concentrated to remove the solvent. The residue is extracted with 500 ml. of hot toluene and the toluene layer is concentrated to a viscous oil which is further purified by HPLC, developed with ethyl acetate to obtain 2-[4-(1H-imidazol-1-yl)-2-butynyl)]-1H-isoindole-1,3(2H)-dione, m.p. 139°-141° C.

Workup

  1. additionA mixture of 27.8 g
  2. concentrationconcentrated
  3. customto remove the solvent
  4. extractionThe residue is extracted with 500 ml
  5. concentrationof hot toluene and the toluene layer is concentrated to a viscous oil which
  6. customis further purified by HPLC

Sources & evidence

ORD record
ord-db9587653fde41139540ca1c9699528b
Source dataset
uspto-grants-1986_02
Patent number
US04568687

Reaction notes

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