Propylene Oxide → N-Chlorophthalimide

HRID 46729

Reaction equation

HRID 46729 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C1OC1C.C(N(C(C)C)CC)(C)C.[Cl:25]Cl>C(Cl)Cl>[Cl:25][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

6

Reactant 4

HCID 6378Propylene OxideHCID 6809PhthalimideHCID 24526ChlorineHCID 81531Diisopropylethylamine

Product 1

HCID 18997N-Chlorophthalimide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 150 ml. of dry methylene chloride were added 7.35 g. (0.05 mole) of phthalimide followed by 17.5 ml. (5 equiv.) of propylene oxide and 0.065 g. (0.5 mmoles) of diisopropylethylamine. The mixture was cooled to 0° C. and saturated with chlorine. The mixture was stirred for about 24 hours to provide approximately 50% conversion to N-chlorophthalimide.

Sources & evidence

ORD record
ord-30bcf861e6db4b1091088b181ae54e82
Source dataset
uspto-grants-1979_11
Patent number
US04175082

Linked notes

Loading…