Sodium Hydroxide → HCID 178510580, compound

HRID 502570Notes

Reaction equation

HRID 502570 reaction equation
[C:1]([C:3]1[C:4]([S:9]CCC(OC)=O)=[N:5][CH:6]=[CH:7][N:8]=1)#[N:2].[OH-].[Na+].[H][H]>O1CCCC1>[SH:9][C:4]1[C:3]([C:1]#[N:2])=[N:8][CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 57436555Methyl 3-[(3-Cyanopyrazin-2-yl)thio]propanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 178510580HCID 178510580, compoundYield 115.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 3-(3-cyanopyrazin-2-ylthio)propanoate (1.56 g, 6.96 mmol) in anhydrous tetrahydrofuran at room temperature was added 60% sodium hydroxide suspension (0.34 g, 8.4 mmol). Vigorous hydrogen evolution was observed. After 1 h at room temperature there appeared to be no reaction, the reaction temperature was raised to 50° C. for 6 h, whereupon the starting material was consumed by TLC. The reaction was quenched by the addition ice, followed by 5% aqueous citric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 3-mercaptopyrazine-2-carbonitrile (1.1 g) as an orange solid. MW=137 confirmed by LC-MS, tr=4.79 min (Method Y) MH+=136-138.

Workup

  1. customno reaction
  2. customwas consumed by TLC
  3. customThe reaction was quenched by the addition ice
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9bdb5f211a754d96a86565640a8e1185
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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