1-Pentanethiol → 2-Cyano-6-pentylthiopyridine

HRID 748193Notes

Reaction equation

HRID 748193 reaction equation
[CH2:1]([SH:6])[CH2:2][CH2:3][CH2:4][CH3:5].[H-].[Na+].Cl[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[N:11]=1>O1CCCC1>[C:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([S:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[N:11]=1)#[N:17]

Participants

5

Reactant 3

HCID 80671-PentanethiolHCID 24758Sodium hydrideHCID 1184246-Chloropyridine-2-carbonitrile

Product 1

HCID 229392832-Cyano-6-pentylthiopyridineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Pentyl mercaptan (0.83 g, 7.9 mmol) was dissolved in tetrahydrofuran (100 ml) and added dropwise to sodium hydride (60% oil, 0.35 g, 8.7 mmol). The reaction mixture was stirred at room temperature for 1 hr. A solution of 2-chloro-6-cyanopyridine (1.00 g, 7.2 mmol) in tetrahydrofuran (10 ml) was added to the mixture, and the mixture was stirred at room temperature for 18 hrs. The reaction mixture was concentrated under reduced pressure, diluted with water and extracted with ethyl acetate. The extract was washed with saturated brine and dried. The solvent was evaporated under reduced pressure to give the titled compound (1.48 g, ca. 100%) as an oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. customdried
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-960a4b4dba324bd5ae9ad4148c8f6267
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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