Dimethylformamide → 3-Bromo-5-(ethylthio)pyridine

HRID 2297964Notes

Reaction equation

HRID 2297964 reaction equation
[OH-].[Na+].CN(C=O)C.[CH2:8]([SH:10])[CH3:9].Br[C:12]1[CH:13]=[N:14][CH:15]=[C:16]([Br:18])[CH:17]=1>O>[Br:18][C:16]1[CH:15]=[N:14][CH:13]=[C:12]([S:10][CH2:8][CH3:9])[CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6343EthanethiolHCID 14798Sodium Hydroxide2×HCID 693693,5-Dibromopyridine

Product 1

HCID 186245803-Bromo-5-(ethylthio)pyridineYield 80.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, NaOH (1.25 g, 31.3 mmol) was added to anhydrous DMF (40 mL). Ethanethiol (2.60 mL, 2.20 g, 35.5 mmol) was then added by syringe and the mixture was stirred for 6 h at 25° C. while the NaOH dissolved. The solution was cooled to 0° C., and 3,5-dibromopyridine (5.92 g, 25.0 mmol) was added. After stirring for 15 min at 0° C. and 45 min at 25° C., the mixture was poured into water (250 mL) and extracted with ether (2×100 mL). Drying (Na2SO4) and evaporation of the ether, followed by vacuum distillation of the crude product gave 4.39 g (80.6% yield) of colorless oil, bp 91-95° C. at 0.30 mm Hg.

Workup

  1. dissolutiondissolved
  2. extractionextracted with ether (2×100 mL)
  3. customDrying
  4. custom(Na2SO4) and evaporation of the ether
  5. distillationfollowed by vacuum distillation of the crude product

Sources & evidence

ORD record
ord-b140ee4a832a475295eaabf6d4cbff64
Source dataset
uspto-grants-2002_12
Patent number
US06492399B1

Reaction notes

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