1-Propanethiol, sodium salt (1:1) → HCID 59497131, compound

HRID 2046518Notes

Reaction equation

HRID 2046518 reaction equation
[CH2:1]([S-:4])[CH2:2][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][CH2:1][CH2:2][CH3:3])[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 46817251-Propanethiol, sodium salt (1:1)HCID 59497129HCID 59497129, compound

Product 1

HCID 59497131HCID 59497131, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Solid sodium 1-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 and allowed to reach room temperature. 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 solid residue was treated with ethyl ether, filtered, and dried yielding 0.98 g of a dark orange solid (76%).

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hours
  2. customto reach room temperature
  3. customThe solvent was removed in a rotary evaporator
  4. additionthe residue was treated with methylene choride (100 mL) and saturated NaHCO3 (100 mL)
  5. customtransferred to a separatory funnel
  6. washThe organic layer was washed with brine (100 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. additionThe solid residue was treated with ethyl ether
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-3c061a8143b04104a6c725ed3705e088
Source dataset
uspto-grants-2013_11
Patent number
US08592446B2

Reaction notes

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