Sodium Hydroxide → Sotalol

HRID 1534563

Reaction equation

HRID 1534563 reaction equation
[CH3:1][CH:2]([NH:4][CH2:5][CH:6]([OH:18])[C:7]1[CH:8]=[CH:9][C:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][CH:12]=1)[CH3:3].Cl.[OH-].[Na+]>C(O)C.C(#N)C>[CH3:3][CH:2]([NH:4][CH2:5][CH:6]([OH:18])[C:7]1[CH:8]=[CH:9][C:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][CH:12]=1)[CH3:1]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66245959-24-0

Product 1

HCID 5253Sotalol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

--A solution of racemic sotalol (24.5 g., 0.09 mole) (obtained by neutralizing sotalol hydrochloride in ethanol with a mole equivalent of concentrated sodium hydroxide, concentration and extraction of the free base in acetonitrile) in 200 ml. of hot isopropanol was mixed with 13.7 g (0.09 mole) of 1-mandelic acid. On cooling, an optically enriched fraction, 26.0 g., m.p. 125-140°, [α]D25 -27.2°, of the d-sotalol·1-mandelate salt was obtained. Crystallization from isopropanol (300 ml.) afforded 18.7 g., m.p. 139-145.5°, [α]D25 -25.4°. Further recrystallization of this material from 1:1 isopropanol-absolute ethanol provided d-sotalol.1-mandelate as white fluffy needles, m.p. 154.5≥156°, [α]D25 -14. 2°.

Sources & evidence

ORD record
ord-692c61abf3044e2dac3ef07951129356
Source dataset
uspto-grants-1992_02
Patent number
US05089526

Linked notes

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