N,N-Diethylethylenediamine → 4-[7-Chloro-4-cinnolinylamino]-N-(2-diethylaminoethyl)benzenesulphonamide

HRID 1383068Notes

Reaction equation

[Na].[CH2:2]([N:4]([CH2:8][CH3:9])[CH2:5][CH2:6][NH2:7])[CH3:3].Cl.[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([C:16]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=3)=[CH:17][N:18]=[N:19]2)=[CH:14][CH:13]=1>C(Cl)(Cl)Cl>[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([C:16]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([S:29]([NH:7][CH2:6][CH2:5][N:4]([CH2:8][CH3:9])[CH2:2][CH3:3])(=[O:30])=[O:31])=[CH:27][CH:28]=3)=[CH:17][N:18]=[N:19]2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A mixture of anhydrous sodium carbonte (3.08 g) and N,N-diethylethylenediamine (0.43 ml) in chloroform (30 ml) was vigorously stirred at 5° C. and treated with 4-(7-Chloro-4-cinnolinylamino)benzenesulphonyl chloride hydrochloride (1.0 g). The mixture was stirred at room temperature for 11/2 hours and then filtered. The filtrate was evaporated to give a residue that crystallised from ethanol to give the title compound (0.456 g), m.p. 175°-76° C.

Workup

stirringThe mixture was stirred at room temperature for 11/2 hours
filtrationfiltered
customThe filtrate was evaporated
customto give a residue that
customcrystallised from ethanol

Sources & evidence

ORD record: ord-b42010eb0bd942fda865ddaacc42ce47
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04808715

Reaction notes

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