Sodium Hydroxide → Sodium 2-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-3-oxo-4,4-dipropyl-3,4-dihydro-1-naphthalenolate

HRID 2224762Notes

Reaction equation

HRID 2224762 reaction equation
[O:1]=[S:2]1(=[O:30])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]([C:12]2[C:13](=[O:29])[C:14]([CH2:26][CH2:27][CH3:28])([CH2:23][CH2:24][CH3:25])[C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:3]1.[OH-].[Na+:32]>C(#N)C.O>[O:30]=[S:2]1(=[O:1])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]([C:12]2[C:13](=[O:29])[C:14]([CH2:26][CH2:27][CH3:28])([CH2:23][CH2:24][CH3:25])[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]=2[O-:22])=[N:3]1.[Na+:32]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1355144473-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1,1-dipropyl-2(1H)-naphthalenone

Product 1

HCID 68874500Sodium 2-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-3-oxo-4,4-dipropyl-3,4-dihydro-1-naphthalenolateYield 101.6%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

A suspension of the product of Example 1H (55 mg, 0.13 mmol) in 1:1 acetonitrile-water was treated with 1N NaOH solution (130 μL 0.13 mmol) and stirred at 25° C. for 2 hours. The solution was then lyophilized to afford the title compound (59 mg, 100%) a fluffy white solid. 1H NMR (300 MHz, DMSO-d6): δ 5.52 (s, 1 H), 8.06 (d, J=7.72 Hz, 1 H), 7.64 (d, J=7.72 Hz, 1 H), 7.49 (m, 3 H), 7.30 (m, 3 H), 2.10 (m, 2 H), 1.67 (m, 2 H), 0.88 (m, 2 H), 0.59 (m, 8 H).

Sources & evidence

ORD record
ord-0b88c83b395c4dd6a0ae8d86b96de5e7
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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