Phosphorus sulfide (P2S5) → 4-Thioacetamidophenethyl Acetate

HRID 369565Notes

Reaction equation

HRID 369565 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=O)[CH3:15])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:18]>C1(C)C=CC=CC=1>[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[S:18])[CH3:15])=[CH:9][CH:8]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 125713974-Acetamidophenethyl acetate

Product 1

HCID 232822924-Thioacetamidophenethyl AcetateYield 142.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Acetamidophenethyl acetate (10.0 g, 45.2 mmol) and phosphorus pentasulfide (10.0 g, 22.5 mmol) were suspended in toluene (200 ml). The suspension was refluxed for 40 min. After cooling the supernatant was decanted into a separatory funnel and washed with 50% aqueous Na2CO3 solution (70 ml) and then with water (70 ml). The organic toluene layer was dried over anhydrous sodium sulfate overnight. The dried toluene solution was concentrated to dryness to give a yellowish solid (7.6 g, 71%). This solid was used for next reaction without further purification.

Workup

  1. temperatureThe suspension was refluxed for 40 min
  2. temperatureAfter cooling the supernatant
  3. customwas decanted into a separatory funnel
  4. washwashed with 50% aqueous Na2CO3 solution (70 ml)
  5. dry with materialThe organic toluene layer was dried over anhydrous sodium sulfate overnight
  6. concentrationThe dried toluene solution was concentrated to dryness

Sources & evidence

ORD record
ord-f4daf685128d4de4bd28c30416207fa9
Source dataset
uspto-grants-2000_10
Patent number
US06140051

Reaction notes

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