Cyclohexyl bromide → 2-Cyclohexylsulfanyl-nicotinic acid

HRID 62865

Reaction equation

HRID 62865 reaction equation
[SH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[H-].[Na+].Br[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>CN(C=O)C>[CH:14]1([S:1][C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 7960Cyclohexyl bromideHCID 24758Sodium hydrideHCID 178524460HCID 178524460, compound

Product 1

HCID 287388022-Cyclohexylsulfanyl-nicotinic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Mercapto-nicotinic acid (0.5 g, 3.22 mmol) was dissolved in DMF (5 mL), and the solution was cooled to 0˜5° C. NaH (0.64 g, 16.11 mmol) was added slowly thereto, and the mixture was stirred at 0˜5° C. for 30 minutes. Bromo-cyclohexane (1.19 mL, 9.66 mmol) was added thereto, and the mixture was stirred at room temperature for 12 hours. After the termination of the reaction, the reactant was concentrated under reduced pressure, and the residue was diluted with water. 3N HCl was used to adjust the pH of the solution to 2˜3, and the solution was extracted with EtOAc. The organic layer was dried with MgSO4 and concentrated under reduced pressure to obtain the title compound, which was used in the next step without a separate purification process.

Workup

  1. temperaturethe solution was cooled to 0˜5° C
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. customAfter the termination of the reaction
  4. concentrationthe reactant was concentrated under reduced pressure
  5. additionthe residue was diluted with water
  6. extractionthe solution was extracted with EtOAc
  7. dry with materialThe organic layer was dried with MgSO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c254a23b3b1a4858b03651e3dddb1ae7
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Linked notes

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