Propyl mercaptan → HCID 15136157, compound

HRID 1651047Notes

Reaction equation

HRID 1651047 reaction equation
[H-].[Na+].C(S)CC.[CH2:7]([O:9][C:10]([C:12]1[C:21](=[O:22])[N:20]2[C:15]([C:16]([S:23]C(=O)N(C)C)=[CH:17][CH:18]=[CH:19]2)=[CH:14][CH:13]=1)=[O:11])[CH3:8].Cl[O-].[Na+]>O1CCCC1>[CH2:7]([O:9][C:10]([C:12]1[C:21](=[O:22])[N:20]2[C:15]([C:16]([SH:23])=[CH:17][CH:18]=[CH:19]2)=[CH:14][CH:13]=1)=[O:11])[CH3:8]

Participants

6

Reactant 4

HCID 7848Propyl mercaptanHCID 24758Sodium hydrideHCID 15136163HCID 15136163, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 15136157HCID 15136157, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.395 g of 60% sodium hydride (mineral oil dispersion) in 20 ml of anhydrous tetrahydrofuran is added 0.82 ml of n-propyl mercaptan under ice-cooling. After stirring for 30 minutes, the resultant mixture is mixed with 2.634 g of 3-ethoxycarbonyl-9-dimethylcarbamoylthio-4H-quinolizin-4-one in 40 ml of tetrahydrofuran, and stirred at room temperature for another 15 hours. The reaction mixture is mixed with 8 ml of aqueous sodium hypochlorite and extracted with methylene chloride. The organic layer is washed with water, dried over sodium sulfate and concentrated to give a residue, which is chromatographed on a column of 30 g of silica gel eluting with methylene chloride-methanol (9:1 v/v) to give crude product, which is recrystallized from ethyl acetate to give 1.153 g (Yield: 56.3%) of 3-ethoxycarbonyl-9-mercapto-4H-quinolizin-4-one.

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature for another 15 hours
  3. extractionextracted with methylene chloride
  4. washThe organic layer is washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give a residue, which
  8. customis chromatographed on a column of 30 g of silica gel eluting with methylene chloride-methanol (9:1 v/v)
  9. customto give crude product, which
  10. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-cc37d8af642347a194f5a374ea6ac4ac
Source dataset
uspto-grants-1990_05
Patent number
US04927829

Reaction notes

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