2-Aminobenzenesulfonamide → 1-butyl-3-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-methylnaphthalen-2(1H)-one

HRID 2224844Notes

Reaction equation

CS[C:3](SC)=[C:4]1[C:13](=[O:14])[C:12]([CH2:16][CH2:17][CH2:18][CH3:19])([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:20].[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30]([NH2:33])(=[O:32])=[O:31]>C1(C)C=CC=CC=1>[CH2:16]([C:12]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:20])=[C:4]([C:3]2[NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[S:30](=[O:31])(=[O:32])[N:33]=2)[C:13]1=[O:14])[CH2:17][CH2:18][CH3:19]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of Example 27F (0.064 g, 0.191 mmol) and 2-amino-benzenesulfonamide (0.035 g, 0.201 mmol) in toluene (7 mL) was refluxed for 6 hours. The solution was cooled to 25° C. and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane followed by 20% and 30% ethyl acetate in hexane to give the desired product (0.067 g, 86%).

Workup

concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel eluting with hexane

Sources & evidence

ORD record: ord-04809c1b967f4855ad44cb8b9eaf0504
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378414B2

Reaction notes

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