Sodium Hydroxide → Sodium 4-(5,5-dimethylhexyl)-2-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-methyl-3-oxo-3,4-dihydronaphthalen-1-olate

HRID 494541Notes

Reaction equation

HRID 494541 reaction equation
[CH3:1][C:2]([CH3:33])([CH3:32])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1([CH3:31])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[C:9]([C:18]2[NH:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[S:20](=[O:29])(=[O:28])[N:19]=2)[C:8]1=[O:30].[OH-].[Na+:35]>O>[CH3:1][C:2]([CH3:33])([CH3:32])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1([CH3:31])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O-:17])=[C:9]([C:18]2[NH:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[S:20](=[O:29])(=[O:28])[N:19]=2)[C:8]1=[O:30].[Na+:35]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1354810131-(5,5-Dimethylhexyl)-3-(1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-methylnaphthalen-2(1h)-one

Product 1

HCID 68874343Sodium 4-(5,5-dimethylhexyl)-2-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-methyl-3-oxo-3,4-dihydronaphthalen-1-olateYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of the product of Example 35I (0-99 g) in water (2 mL) was treated with 0.997N sodium hydroxide solution (0.213 mL, 0.212 mmol) and stirred at 25° C. for 1 hour. The solution was lyophilized to give the title compound (0.104 g, 99%). 1H NMR (300 MHz, DMSO-d6): δ ppm 0.59 (m, 1 H) 0.74 (m, 9 H) 0.95 (m, 5 H) 1.39 (m, 3 H) 1.72 (m, 1 H) 2.14 (m, 1 H) 7.30 (m, 3 H) 7.50 (m, 3 H) 7.65 (m, 1 H) 8.05 (m, 1 H) 15.45 (m, 1 H). MS (ESI−) m/z 465 (M−H)−.

Sources & evidence

ORD record
ord-5b665bdcbd9740d19e198afa95462f30
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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