2-Aminobenzenesulfonamide → 1-(5,5-Dimethylhexyl)-3-(1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-methylnaphthalen-2(1h)-one

HRID 494540Notes

Reaction equation

HRID 494540 reaction equation
CS[C:3](SC)=[C:4]1[C:13](=[O:14])[C:12]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[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>[CH3:22][C:20]([CH3:23])([CH3:21])[CH2:19][CH2:18][CH2:17][CH2:16][C:12]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[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]

Participants

4

Reactant 2

HCID 728942-AminobenzenesulfonamideHCID 113038662-[Bis(methylthio)methylene]-4-(5,5-dimethylhexyl)-4-methylnaphthalene-1,3(2h,4h)-dione

Product 1

HCID 1354810131-(5,5-Dimethylhexyl)-3-(1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-methylnaphthalen-2(1h)-oneYield 852.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of Example 35H (0.097 g, 0.249 mmol) and 2-amino-benzenesulfonamide (0.045 g, 0.262 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 (0.99 g, 85%).

Workup

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

Sources & evidence

ORD record
ord-be379cd4ff9a4bae972b1caed13d7c88
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

Loading…