1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → Phthalimide

HRID 367220Notes

Reaction equation

HRID 367220 reaction equation
[H-].[Li+].ClC1C=CC(NC2SC3N=CC=CC=3C(=O)N=2)=CC=1.BrCC[N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35]>CN(C=O)C>[C:26]1(=[O:35])[C:27]2[C:28](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](=[O:30])[NH:25]1

Participants

5

Reactant 3

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 62714Lithium hydrideHCID 42920704H-Pyrido[3,2-e]-1,3-thiazin-4-one, 2-[(4-chlorophenyl)amino]-

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction and processing procedure of Example 127 was followed except that 30 mg (3.8 mmol) of lithium hydride, 17 ml of DMF, 800 mg (2.8 mmol) of 2-(4-chloroanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one and 1.12 g of N-(2-bromoethyl)-phthalimide were used and post-treatment was carried out. The resulting residue was then purified through silica gel column chromatography (eluant: 1/2 mixture of ethyl acetate and normal hexane) to obtain 883 mg of 2-[2-[2-(4-chlorophenyl)imino]-4-oxo-2,3-dihydro-4H-pyrido[3,2-e]-1,3-thiazin-3-yl]ethyl]isoindol-1,3-dione.

Workup

  1. customThe reaction and processing procedure of Example 127
  2. customThe resulting residue was then purified through silica gel column chromatography (eluant: 1/2 mixture of ethyl acetate and normal hexane)

Sources & evidence

ORD record
ord-92b2435a84c943a6af7c06d8587a42d4
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

Loading…