N,N-Dimethyl-1,3-propanediamine → Phthalimide

HRID 2164548Notes

Reaction equation

HRID 2164548 reaction equation
Cl[C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:18])[N:7](CCCN(C)C)[C:8]2=[O:11])=[CH:4][C:3]=1S(N)(=O)=O.ClC1C=C2C(=O)NC(=O)C2=CC=1S(=O)(=O)N.CN(C)CCCN>>[O:18]=[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 7993N,N-Dimethyl-1,3-propanediamineHCID 197334-(Aminosulfonyl)-5-chlorophthalimideHCID 13473190HCID 13473190, compound

Product 1

HCID 6809PhthalimideYield 95%

Procedure

6-Chloro-2-[3-(dimethylamino)propyl]-2,3-dihydro-1,3-dioxo-1H-isoindole-5-sulfonamide. Reaction of a mixture 4-chloro-5-sulfamoylphthalimide and 3-(dimethylamino)propylamine according to the procedure of Example 1(a) afforded a 95% yield of the 1,3-dioxoisoindole intermediate. Crystallization of this material from dimethylformamide-ethanol provided analytically pure 6-chloro-2-[3-(dimethylamino)propyl]-2,3-dihydro-1,3-dioxo-1H-isoindole-5-sulfonamide, m.p. 192°-194°.

Sources & evidence

ORD record
ord-2f5866d8ff044024aae32e7076aec5eb
Source dataset
uspto-grants-1985_03
Patent number
US04505911

Reaction notes

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