Benzenesulfonyl chloride → N-(4-Chloro-quinolin-8-yl)-benzenesulfonamide

HRID 513435Notes

Reaction equation

HRID 513435 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([NH2:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([NH:12][S:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)(=[O:21])=[O:20])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 126042744-Chloroquinolin-8-amine

Product 1

HCID 68183402N-(4-Chloro-quinolin-8-yl)-benzenesulfonamideYield 61.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar fashion using route 14 general procedure 26, 4-chloro-quinolin-8-ylamine 464 (228 mg, 1.28 mmol), benzenesulfonyl chloride (0.2 ml, 1.53 mmol) pyridine (0.21 ml, 2.56 mmol) in DCM (10 ml) gave the title compound (250 mg, 61%) after purification by column chromatography with DCM/MeOH (99:1) as the eluent.

Sources & evidence

ORD record
ord-dbf80136288040ceab2bd36e03d931ce
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…