o-Toluenesulfonyl chloride → HCID 49766557, compound

HRID 513440Notes

Reaction equation

HRID 513440 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])[C:13]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=1>CN(C1C=CN=CC=1)C.CCCCCC>[CH3:22][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18]([NH: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)(=[O:20])=[O:19]

Participants

5

Reactant 2

HCID 8623o-Toluenesulfonyl chlorideHCID 113598-Aminoquinoline

Product 1

HCID 49766557HCID 49766557, compoundYield 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), o-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-15aeaca8e3124309993b4a07145952d8
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

Loading…