4-(Aminosulfonyl)-5-chlorophthalimide → Phthalimide

HRID 2164546Notes

Reaction equation

HRID 2164546 reaction equation
Cl[C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:21])[N:7](CCCN3CCOCC3)[C:8]2=[O:11])=[CH:4][C:3]=1S(N)(=O)=O.ClC1C=C2C(=O)NC(=O)C2=CC=1S(=O)(=O)N.NCCCN1CCOCC1>>[O:21]=[C:6]1[C:5]2[C:9](=[CH:10][CH:2]=[CH:3][CH:4]=2)[C:8](=[O:11])[NH:7]1

Participants

4

Reactant 3

HCID 197334-(Aminosulfonyl)-5-chlorophthalimideHCID 61055N-(3-Aminopropyl)morpholineHCID 13473188HCID 13473188, compound

Product 1

HCID 6809PhthalimideYield 92%

Procedure

6-Chloro-2,3-dihydro-2-[3-(4-morpholinyl)propyl]-1,3-dioxo-1H-isoindole-5-sulfonamide. Reaction of a mixture of 4-chloro-5-sulfamoylphthalimide and N-(3-aminopropyl)morpholine according to the procedure of Example 1(a) afforded a 92% yield of the 1,3-dioxoisoindole intermediate. Crystallization of this material from 80% aqueous ethanol provided analytically pure 6-chloro-2,3-dihydro-2-[3-(4-morpholinyl)propyl]-1,3-dioxo-1H-isoindole-5-sulfonamide, m.p. 190°-191°.

Sources & evidence

ORD record
ord-8986b95ece0443b2af887de63f611e1e
Source dataset
uspto-grants-1985_03
Patent number
US04505911

Reaction notes

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