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

HRID 2224809Notes

Reaction equation

HRID 2224809 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-72a70878b7724dcf8f9f7f7a3afe4f37
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

Loading…