Sodium methanethiolate → HCID 89996128, compound

HRID 1480829Notes

Reaction equation

HRID 1480829 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.[CH3:13][S-:14].[Na+]>C(#N)C.CN(C=O)C>[CH3:9][O:8][C:6]1[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=[C:2]([S:14][CH3:13])[N:7]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 107977036-Chloro-2-methoxy-3-nitropyridine

Product 1

HCID 89996128HCID 89996128, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

To a solution of 6-chloro-2-methoxy-3-nitropyridine (300 mg, 1.591 mmol) in acetonitrile/DMF (2:1, 3 mL) was added sodium thiomethoxide (133 mg, 1.91 mmol). The reaction mixture was stirred at room temperature for 18 hours and then concentrated in vacuo. The residue was partitioned between water (30 mL) and EtOAc (30 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to give the title compound (290 mg, 91%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between water (30 mL) and EtOAc (30 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70f6c276ae1f4cdc8597884215f0287e
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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