Phosphorus sulfide (P2S5) → HCID 178446957, compound

HRID 1670525Notes

Reaction equation

HRID 1670525 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:4][N:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:15]>N1C=CC=CC=1>[SH:15][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 178446955HCID 178446955, compound

Product 1

HCID 178446957HCID 178446957, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

Combine 2-hydroxy-5-(3-methyl-butyryl)-pyridine (742 mg, 4.1 mmol) and phosphorus pentasulfide (1.88 g, 4.2 mmol) in pyridine (5 mL). Heat the mixture at 120° C. for 5 h under a nitrogen atmosphere. Cool the mixture to room temperature and partition between water and EtOAc. Collect the aqueous layer, wash with additional EtOAc and DCM. Acidify the aqueous layer with 1M aqueous HCl and extract with DCM (4×30 mL). Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo to obtain the title compound (120 mg, 15%). MS (ES+) m/z: 196.2 (M+H)+.

Workup

  1. temperatureCool the mixture to room temperature
  2. custompartition between water and EtOAc
  3. customCollect the aqueous layer
  4. washwash with additional EtOAc and DCM
  5. extractionextract with DCM (4×30 mL)
  6. dry with materialDry the combined organic extracts over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-ccfadaeb5214486ab8401679cf47eb9a
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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