4-Toluenesulfonyl chloride → Benzenesulfonamide, 4-methyl-N-8-quinolinyl-

HRID 513439Notes

Reaction equation

HRID 513439 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>CN(C1C=CN=CC=1)C.CCCCCC>[CH3:22][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 113598-Aminoquinoline

Product 1

HCID 82533Benzenesulfonamide, 4-methyl-N-8-quinolinyl-Yield 64.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8058HexaneSolvent

Procedure

In the similar fashion using route 14 general procedure 27, 8-aminoquinoline (200 mg, 1.38 mmol), p-toluenesulfonyl chloride (260 mg, 1.3 mmol) and DMAP (cat.) gave the title compound (250 mg, 60%) after trituration from n-hexane.

Sources & evidence

ORD record
ord-df1a36a76a5e434984711efcec1aba52
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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