Sodium 2-propanethiolate → HCID 59497127, compound

HRID 2046522Notes

Reaction equation

HRID 2046522 reaction equation
[CH3:1][CH:2]([S-:4])[CH3:3].[Na+].Cl[C:7]1[C:20]2[C:11](=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[CH:15][CH:14]=[N:13]3)[N:10]=[C:9]([CH3:21])[CH:8]=1>CO>[CH3:21][C:9]1[CH:8]=[C:7]([S:4][CH:2]([CH3:3])[CH3:1])[C:20]2[C:11](=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH:16]=[CH:15][CH:14]=[N:13]3)[N:10]=1

Participants

4

Reactant 2

HCID 3470666Sodium 2-propanethiolateHCID 59497129HCID 59497129, compound

Product 1

HCID 59497127HCID 59497127, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Solid sodium 2-propanethiolate (2.35 g, 24.0 mmol) was added to a 100 mL round-bottomed flask containing a solution of 4-chloro-2-methyl-[1,10]phenanthroline (1.10 g, 4.8 mmol) in methanol (50 mL). The reaction mixture was refluxed for 18 hours. The solvent was removed in a rotary evaporator and the residue was treated with methylene choride (100 mL) and saturated NaHCO3 (100 mL) and transferred to a separatory funnel. The organic layer was washed with brine (100 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, MeOH/DCM, 1:80) to afford the pure product as a yellow oil (1.03 g, 80%).

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hours
  2. customThe solvent was removed in a rotary evaporator
  3. additionthe residue was treated with methylene choride (100 mL) and saturated NaHCO3 (100 mL)
  4. customtransferred to a separatory funnel
  5. washThe organic layer was washed with brine (100 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (SiO2, MeOH/DCM, 1:80)

Sources & evidence

ORD record
ord-4ad6aa94ed05459cbe40549af50dbe90
Source dataset
uspto-grants-2013_11
Patent number
US08592446B2

Reaction notes

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