2-Propanethiol → HCID 22939361, compound

HRID 499372Notes

Reaction equation

HRID 499372 reaction equation
[CH:1]([SH:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[N:9]=1>O1CCCC1>[C:14]([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([S:4][CH:1]([CH3:3])[CH3:2])[N:9]=1)#[N:15]

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 24758Sodium hydrideHCID 1184246-Chloropyridine-2-carbonitrile

Product 1

HCID 22939361HCID 22939361, compoundYield 109.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Isopropyl mercaptan (0.60 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 (1.40 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-efe2d2d6d53e4af88ad1f342563bb8a6
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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