2-Propanethiol → HCID 22939361, compound

HRID 748189Notes

Reaction equation

HRID 748189 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-e5a336056b6c4d269247abbd04a769d2
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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