Benzenesulfonyl chloride → N-(2-Chloroquinolin-8-yl)-benzenesulfonamide

HRID 513468Notes

Reaction equation

HRID 513468 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH2:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[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]2[C:4](=[C:5]([NH:12][S:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)(=[O:21])=[O:20])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 3465192-Chloroquinolin-8-amine2×

Product 1

HCID 86669756N-(2-Chloroquinolin-8-yl)-benzenesulfonamideYield 88.5%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In the similar fashion using route 14 general procedure 27, 2-chloroquinolin-8-amine (Intermediate 26) (70 mg, 0.39 mmol), benzenesulfonyl chloride (83 mg, 0.42 mmol) and DMAP (cat.) gave the title compound (110 mg, 88%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-7e15a17fd9cc4e70b07365bb593ad043
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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