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

HRID 2224845Notes

Reaction equation

HRID 2224845 reaction equation
[CH2:1]([C:5]1([CH3:29])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[S:18](=[O:27])(=[O:26])[N:17]=2)[C:6]1=[O:28])[CH2:2][CH2:3][CH3:4].[OH-].[Na+:31]>O>[CH2:1]([C:5]1([CH3:29])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O-:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[S:18](=[O:26])(=[O:27])[N:17]=2)[C:6]1=[O:28])[CH2:2][CH2:3][CH3:4].[Na+:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1354233131-butyl-3-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-methylnaphthalen-2(1H)-one

Product 1

HCID 68870279Sodium 4-butyl-2-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-methyl-3-oxo-3,4-dihydronaphthalen-1-olateYield 99.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of the product of Example 30A (0.067 g) in water (2 mL) was treated with 0.997N sodium hydroxide solution (0.163 mL, 0.163 mmol) and stirred at 25° C. for 1 hour. The solution was lyophilized to give the title compound (0.070 g, 99%). 1H NMR (300 MHz, DMSO-d6): δ ppm 0.55 (m, 1 H) 0.68 (m, 3 H) 0.87 (m, 1 H) 1.06 (m, 2 H) 1.38 (m, 3 H) 1.72 (m, 1 H) 2.13 (m, 1 H) 7.29 (m, 3 H) 7.49 (m, 3 H) 7.64 (m, 1 H) 8.05 (m, 1 H) 15.46 (m, 1 H). MS (ESI−) m/z 409 (M−H)−.

Sources & evidence

ORD record
ord-3d9551ce3c284cb893028fb5974c2228
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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