Phosphorus sulfide (P2S5) → HCID 178527857, compound

HRID 1904642Notes

Reaction equation

HRID 1904642 reaction equation
[CH2:1]([C:8]1[C:9](=O)[NH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:16]>N1C=CC=CC=1.[Cl-].[Na+].O>[CH2:1]([C:8]1[C:9]([SH:16])=[N:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 10877818HCID 10877818, compound

Product 1

HCID 178527857HCID 178527857, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3-Benzyl-2-pyridone (1.65g, 8.9 mmol) and P2S5 (1.98 g, 8.9 mmol) were heated at reflux for 22 hours under argon in pyridine (17ml), and then allowed to stand overnight at ambient temperature. The mixture was diluted with brine and extracted with ethyl acetate. The ethyl acetate extracts were dried (MgSO4) and purified by chromatography using 5% CH3OH--CH2Cl2 as eluant followed by recrystallization from CH2Cl2 --ether--hexane to yield 300 mg (15%) of 3-benzyl-2-mercaptopyridine: m.p. 129°-130° C. That the 3-benzyl isomer had been isolated was confirmed by use of proton NMR spectroscopy.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate extracts were dried (MgSO4)
  3. custompurified by chromatography
  4. customCH2Cl2 as eluant followed by recrystallization from CH2Cl2

Sources & evidence

ORD record
ord-189ed575ff514d7782fb313c7cc637e8
Source dataset
uspto-grants-1989_06
Patent number
US04839371

Reaction notes

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