2,5-Dimethoxyaniline → n-[3-(2,5-Dimethoxy-phenylamino)-quinoxalin-2-yl]-3-fluorobenzenesulfonamide

HRID 655631Notes

Reaction equation

Cl[C:2]1[C:3]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)(=[O:15])=[O:14])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:23][O:24][C:25]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:26]=1[NH2:27]>CCO>[CH3:23][O:24][C:25]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:26]=1[NH:27][C:2]1[C:3]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)(=[O:15])=[O:14])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

Conditions

Temperature: 100 °C

Procedure

N-(3-chloroquinoxalin-2-yl)-3-fluorobenzenesulfonamide (125 mg, 0.4 mmole) and 2,5-dimethoxyaniline (170.4 mg, 1.1 mmole) are taken in 0.5 ml of EtOH and the resulting suspension is stirred at 100° C. in an orbital shaker, overnight. The precipitate obtained is filtered and washed with EtOH then ether to afford the title compound as a dark green solid (163 mg, 97%). HPLC (max plot) 96%, rt. 4.88 min. LC/MS: (ES+): 455.2.

Workup

customThe precipitate obtained
filtrationis filtered
washwashed with EtOH

Sources & evidence

ORD record: ord-91967ea14f7140a1b6d0cfa9cf0bf447
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071597B2

Reaction notes

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