Sodium Bicarbonate → HCID 178482933, compound

HRID 2368532Notes

Reaction equation

HRID 2368532 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][NH:12][C:13](=O)[C:14]([N:16]([CH3:24])[CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[O:15])=[S:10])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]([SH:10])=[N:11][N:12]=[C:13]2[C:14]([N:16]([CH3:24])[CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86677560HCID 86677560, compound

Product 1

HCID 178482933HCID 178482933, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(2-((4-fluorophenyl)carbamothioyl)hydrazinyl)-N-methyl-2-oxo-N-(pyridin-4-ylmethyl)acetamide (79) (0.75 g, 2.075 mmol) and sodium bicarbonate (0.35 g, 4.17 mmol) in methanol/water (1:1) (20 mL) was stirred at 80° C. for 26 h. After evaporation of solvent, the residue was extracted with dichloromethane/methanol (10:1) (3×60 mL). The combined organic phase was evaporated and the crude product was purified by flash column chromatography on silica gel (0%-20% MeOH in dichloromethane) to provide 4-(4-fluorophenyl)-5-mercapto-N-methyl-N-(pyridin-4-ylmethyl)-4H-1,2,4-triazole-3-carboxamide (80) as a white solid (0.11 g).

Workup

  1. customAfter evaporation of solvent
  2. extractionthe residue was extracted with dichloromethane/methanol (10:1) (3×60 mL)
  3. customThe combined organic phase was evaporated
  4. customthe crude product was purified by flash column chromatography on silica gel (0%-20% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-56cf2eb296a24f419f9c9ed0178bc62e
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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