Sodium Hydroxide → Propanoic acid, 2-[[4-(4-cyanophenyl)-3-pyridinyl]thio]-2-methyl-

HRID 45775Notes

Reaction equation

HRID 45775 reaction equation
[OH-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[S:17][C:18]([CH3:25])([CH3:24])[C:19]([O:21]CC)=[O:20])=[CH:7][CH:6]=1)#[N:4]>CO>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[S:17][C:18]([CH3:25])([CH3:24])[C:19]([OH:21])=[O:20])=[CH:9][CH:10]=1)#[N:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67997190HCID 67997190, compound

Product 1

HCID 67997193Propanoic acid, 2-[[4-(4-cyanophenyl)-3-pyridinyl]thio]-2-methyl-Yield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (1 mL) and aqueous sodium hydroxide solution (2M, 1 mL) were added to ethyl 2-(4-(4-cyanophenyl)pyridin-3-ylthio)-2-methylpropanoate (0.25 g, 0.77 mmol) and stirred at ambient temperature for 2 hours. The volume was reduced (˜1 mL) by rotary evaporation and the resulting residue treated with aqueous HCl (6N) with stirring to pH 6, resulting in formation of a white precipitate, which was isolated by filtration. The solid was washed with water (6×1 mL), air dried for 1 hour and dried under vacuum over P2O5 overnight to give a white powder (0.072 g, 32%).

Workup

  1. customby rotary evaporation
  2. additionthe resulting residue treated with aqueous HCl (6N)
  3. stirringwith stirring to pH 6
  4. customresulting in formation of a white precipitate
  5. customwhich was isolated by filtration
  6. washThe solid was washed with water (6×1 mL), air
  7. customdried for 1 hour
  8. dry with materialdried under vacuum over P2O5 overnight

Sources & evidence

ORD record
ord-5ccdbe19050541e9ac1121bad701dfcf
Source dataset
uspto-grants-2013_09
Patent number
US08541589B2

Reaction notes

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