Benzenesulfonyl chloride → N-(5-chloroquinolin-8-yl)benzenesulfonamide

HRID 513469Notes

Reaction equation

HRID 513469 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:21])=[O:20])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 2248605-Chloroquinolin-8-amine2×

Product 1

HCID 3596728N-(5-chloroquinolin-8-yl)benzenesulfonamideYield 64.3%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In the similar fashion using route 14 general procedure 27, 5-chloroquinolin-8-amine (Intermediate 27) (70 mg, 0.39 mmol), benzenesulfonyl chloride (83 mg, 0.42 mmol) and DMAP (cat.) gave the title compound (80 mg, 64%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-69f60a8478cd434d913b9a3827e82611
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…