tert-Butyl mercaptan → HCID 21075124, compound

HRID 499374Notes

Reaction equation

HRID 499374 reaction equation
[C:1](S)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[N:16])[N:10]=1>O1CCCC1>[C:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([C:1]([CH3:4])([CH3:3])[CH3:2])[N:10]=1)#[N:16]

Participants

5

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 24758Sodium hydrideHCID 1184246-Chloropyridine-2-carbonitrile

Product 1

HCID 21075124HCID 21075124, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

tert-Butyl mercaptan (0.72 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 (1.19 g, 86%) 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-e94d1a7c9fc444d6a469d7779ee79a34
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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