Sodium methanethiolate → HCID 86701454, compound

HRID 2173915Notes

Reaction equation

HRID 2173915 reaction equation
Br[C:2]1[CH:9]=[C:8]([CH3:10])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:14][S-:15].[Na+]>CN(C=O)C>[CH3:10][C:8]1[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]([C:4]#[N:5])=[C:2]([S:15][CH3:14])[CH:9]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 57736551HCID 57736551, compound

Product 1

HCID 86701454HCID 86701454, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-bromo-4-methyl-5-nitrobenzonitrile (3 g, 12.45 mmol) in DMF (124 mL), sodium thiomethoxide (1.31 g, 18.67 mmol) was added and the reaction heated to 60° C. for 1 h. The reaction was then cooled to room temperature, quenched with a sat. aq. solution of NaHCO3 and extracted with EtOAc. The organic extract was dried over MgSO4, filtered and concentrated. The resulting residue was purified using FCC eluting with heptanes:EtOAc 1:1 to give the title compound. MS (ESI−) m/z 207.3 (M−H).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. customquenched with a sat. aq. solution of NaHCO3
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified
  9. washeluting with heptanes:EtOAc 1:1

Sources & evidence

ORD record
ord-c8d07fd8bcaf459cb4b1a7ed276bb1e9
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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