Phosphorus sulfide (P2S5) → HCID 3594920, compound

HRID 227250Notes

Reaction equation

HRID 227250 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][C:12](=O)[NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22]>O1CCOCC1>[CH2:1]([N:8]1[CH2:14][CH2:13][C:12](=[S:22])[NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 2397261-benzyl-1,4-diazepan-5-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 3594920HCID 3594920, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 1-benzyl-1,4-diazepan-5-one (2.00 g, 9.80 mmol) in anhydrous dioxane (40 mL), sodium bicarbonate (8.81 g, 105 mmol) and phosphorus pentasulfide (2.92 g, 13.1 mmol) were added. The mixture was heated to 75° C. for 6 h. Dioxane was removed under reduced pressure and the residue was treated with water (80 mL). The resultant mixture was stirred at 50° C. for 1 h and then stirred an additional 2 h at 25° C. Sodium chloride (30.0 g) was added to the mixture and the aqueous phase was extracted with dichloromethane. The organic phase was concentrated to yield the desired compound, which was used without further purification.

Workup

  1. customDioxane was removed under reduced pressure
  2. additionthe residue was treated with water (80 mL)
  3. stirringstirred an additional 2 h at 25° C
  4. additionSodium chloride (30.0 g) was added to the mixture
  5. extractionthe aqueous phase was extracted with dichloromethane
  6. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-34008aba67c5471299066f3acb103938
Source dataset
uspto-grants-2009_07
Patent number
US07560455B2

Reaction notes

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