Sodium Hydroxide → Ethopropazine

HRID 473792Notes

Reaction equation

HRID 473792 reaction equation
[CH3:1][CH2:2][N:3]([CH:6]([CH2:8][N:9]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[S:16][C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2)[CH3:7])[CH2:4][CH3:5].Cl.[OH-].[Na+]>C(Cl)Cl>[CH3:5][CH2:4][N:3]([CH:6]([CH2:8][N:9]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[S:16][C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2)[CH3:7])[CH2:2][CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 122824Ethopropazine hydrochloride

Product 1

HCID 3290EthopropazineYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In other studies, racemic ethopropazine hydrochloride salt was mixed with methylene chloride and 2M sodium hydroxide. The resulting suspension was agitated and the organic layer collected. After drying, the solvent was removed by rotary evaporation to give racemic ethopropazine base (4.0 g, 0.013 mol) that reacted with dibenzoyl-D-tartaric acid (4.4 g, 0.012 mol) in acetone with agitation. A white precipitate was collected after a few hours. After two recrystallization steps from absolute ethanol, a 99+% crystal was obtained, which was converted to ethopropazine hydrochloride salt. Yield: 20%. From the mother liquor, another diastereomeric salt was obtained as white precipitate, which was also recrystalized twice from absolute ethanol before converting to hydrochloride salt. Yield: 20%.

Workup

  1. customthe organic layer collected
  2. customAfter drying
  3. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-111753f8838146109fadd9eb5eed9517
Source dataset
uspto-grants-2014_01
Patent number
US08637503B2

Reaction notes

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