Sodium methanethiolate → HCID 59331532, compound

HRID 1881859Notes

Reaction equation

HRID 1881859 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[CH3:14][S-:15].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:14][S:15][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 15661146Ethyl 2-(6-chloropyridin-3-yl)acetate

Product 1

HCID 59331532HCID 59331532, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl (6-chloropyridin-3-yl)acetate (10.7 g) in N,N-dimethylformamide (100 mL) was added sodium methanethiolate (11.3 g), and the mixture was stirred at room temperature for 23 hr. The reaction mixture was diluted with ethyl acetate, washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-50:50, volume ratio) to give the title compound (4.55 g, yield 40%) as a colorless oil. MS: 212 (MH+).

Workup

  1. washwashed successively with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-50:50, volume ratio)

Sources & evidence

ORD record
ord-6d95e7ac57694ea1bde22f6c0e6b092e
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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