3-Bromopyridine-2-carbonitrile → 3-(Ethylthio)picolinonitrile

HRID 1935453Notes

Reaction equation

HRID 1935453 reaction equation
[CH2:1]([S-:3])[CH3:2].[Na+].Br[C:6]1[C:7]([C:12]#[N:13])=[N:8][CH:9]=[CH:10][CH:11]=1>C1COCC1>[C:12]([C:7]1[C:6]([S:3][CH2:1][CH3:2])=[CH:11][CH:10]=[CH:9][N:8]=1)#[N:13]

Participants

4

Reactant 2

HCID 8176943-Bromopyridine-2-carbonitrileHCID 4459711Sodium ethanethiolate

Product 1

HCID 224645153-(Ethylthio)picolinonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of sodium ethanethiolate (600 mg, 5.75 mmol) in dry THF (25 mL) was added 3-bromo-2-cyanopyridine (700 mg, 3.83 mmol). The reaction mixture was heated to reflux under N2 for 3 h. The solvent was removed in vacuo and the resulting residue was taken Lip in CH2Cl2 (35 mL). The solution was filtered to remove precipitated sodium bromide and the filtrate was concentrated at reduced pressure to afford the title compound as a yellow oil:

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under N2 for 3 h
  3. customThe solvent was removed in vacuo
  4. filtrationThe solution was filtered
  5. customto remove
  6. customprecipitated sodium bromide
  7. concentrationthe filtrate was concentrated at reduced pressure

Sources & evidence

ORD record
ord-d99304f8e1a242cda554d667cdc80967
Source dataset
uspto-grants-2002_05
Patent number
US06387911B1

Reaction notes

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