N-Hydroxyphthalimide → HCID 53700881, compound

HRID 1275371Notes

Reaction equation

HRID 1275371 reaction equation
[Br:1][CH:2]([Br:6])[C:3]([OH:5])=[O:4].O[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].C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[Br:1][CH:2]([Br:6])[C:3]([O:5][N:8]1[C:9](=[O:18])[C:10]2=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]2[C:12]1=[O:13])=[O:4]

Participants

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 10868DicyclohexylcarbodiimideHCID 12433Dibromoacetic Acid

Product 1

HCID 53700881HCID 53700881, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dibromoacetic acid (0.1 mmole) and N-hydroxyphthalimide (0.1 mmole) are mixed and coupled in THF in the presence of DCC for 2 hours. The product, (N-dibromoacetoxyphthalimide) is isolated by filtration and dried. Radical-induced dehalogenation (0.1 mmole scale) using the general method with tributyltin deuteride furnished the N-deuterioacetoxyphthalimide with two atoms of deuterium. The N-ditritioacetoxyphthalimide can be prepared the same way.

Sources & evidence

ORD record
ord-2c714580ef904cb1a849c913a132dab2
Source dataset
uspto-grants-2000_12
Patent number
US06160128

Reaction notes

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