Butyl iodide → 2-Butylsulfanyl-nicotinic acid

HRID 62849Notes

Reaction equation

HRID 62849 reaction equation
[SH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[Na+].I[CH2:14][CH2:15][CH2:16][CH3:17]>CO>[CH2:14]([S:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 14798Sodium HydroxideHCID 178524460HCID 178524460, compound

Product 1

HCID 167837802-Butylsulfanyl-nicotinic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

After MeOH (20 mL) was added to 2-mercapto-nicotinic acid (1 g, 6 mmol), the mixture was cooled to 0° C., and 6 M NaOH aqueous solution (3.2 mL) was added slowly thereto. The reactant was stirred at 0° C. for 30 minutes. 1-Iodobutane (0.74 mL, 6 mmol) was added to the reactant, and the mixture was stirred under reflux at 80° C. for 16 hours. The reactant was concentrated under reduced pressure, and 6 M HCl aqueous solution was added thereto to adjust the pH of the solution to 7. The resulting precipitate was filtered and dried to obtain the title compound (1.27 g, 93%).

Workup

  1. stirringthe mixture was stirred
  2. temperatureunder reflux at 80° C. for 16 hours
  3. concentrationThe reactant was concentrated under reduced pressure, and 6 M HCl aqueous solution
  4. additionwas added
  5. filtrationThe resulting precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-fcf6901b84ec4af59fd8f5051bd6f236
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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