2-Aminobenzenesulfonamide → 1,1-Dibutyl-3-(1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxynaphthalen-2(1h)-one

HRID 494488Notes

Reaction equation

HRID 494488 reaction equation
CS[C:3](SC)=[C:4]1[C:13](=[O:14])[C:12]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:15][CH2:16][CH2:17][CH3:18])[C:11]2[C:6](=[CH:7][C:8]([F:23])=[CH:9][CH:10]=2)[C:5]1=[O:24].[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34]([NH2:37])(=[O:36])=[O:35]>C1(C)C=CC=CC=1>[CH2:15]([C:12]1([CH2:19][CH2:20][CH2:21][CH3:22])[C:11]2[C:6](=[CH:7][C:8]([F:23])=[CH:9][CH:10]=2)[C:5]([OH:24])=[C:4]([C:3]2[NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[S:34](=[O:35])(=[O:36])[N:37]=2)[C:13]1=[O:14])[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 728942-AminobenzenesulfonamideHCID 113838612-[Bis(methylthio)methylene]-4,4-dibutyl-7-fluoronaphthalene-1,3(2h,4h)-dione

Product 1

HCID 1363846071,1-Dibutyl-3-(1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxynaphthalen-2(1h)-oneYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of the compound of Example 18G (39 mg, 0.10 mmol) and 2-aminobenzenesulfonamide (17 mg, 0.10 mmol) in toluene (1 mL) was warmed at reflux for 2 h. The solution was cooled and concentrated in vacuo to afford a yellow foam which was purified by flash chromatography eluting with ethyl acetate in hexane to afford the title compound (33 mg, 0.07 mmol)

Workup

  1. temperaturewas warmed
  2. temperatureat reflux for 2 h
  3. temperatureThe solution was cooled
  4. concentrationconcentrated in vacuo
  5. customto afford a yellow foam which
  6. customwas purified by flash chromatography
  7. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-c858528d31334e27b47e6f8f4a678be7
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

Loading…