4-(Aminosulfonyl)-5-chlorophthalimide → Phthalimide

HRID 2164547Notes

Reaction equation

HRID 2164547 reaction equation
Cl[C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:19])[N:7](CCN(CC)CC)[C:8]2=[O:11])=[CH:4][C:3]=1S(N)(=O)=O.ClC1C=C2C(=O)NC(=O)C2=CC=1S(=O)(=O)N.C(N(CC)CCN)C>>[O:19]=[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 60993N,N-DiethylethylenediamineHCID 13473189HCID 13473189, compound

Product 1

HCID 6809PhthalimideYield 50%

Procedure

6-Chloro-2-[2-(diethylamino)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindole-5-sulfonamide. Reaction of a mixture of 4-chloro-5-sulfamoylphthalimide and 2-(diethylamino)ethylamine according to the procedure of Example 1(a) afforded a 50% yield of the 1,3-dioxoisoindole intermediate. Crystallization of this material from dimethylformamide-ethanol provided analytically pure 6-chloro-2-[2-(diethylamino)ethyl]-2,3-dihydro-1,3-dioxo-1H-isoindole-5-sulfonamide, m.p. 152°-154°.

Sources & evidence

ORD record
ord-e5994e838e7c410182031301b6a2c576
Source dataset
uspto-grants-1985_03
Patent number
US04505911

Reaction notes

Loading…