Phosphorus sulfide (P2S5) → HCID 21836471, compound

HRID 726128Notes

Reaction equation

HRID 726128 reaction equation
[F:1][C:2](=[C:13]([F:15])[F:14])[CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:17]>C1COCC1>[F:1][C:2](=[C:13]([F:15])[F:14])[CH2:3][C:4](=[S:17])[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 21836474HCID 21836474, compound

Product 1

HCID 21836471HCID 21836471, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3,4,4-trifluoro-N-phenyl-3-butenamide (1.0 g, 4.65 mmol) and phosphorus pentasulfide (2.07 g, 4.65 mmol) in anhyd. THF (100 mL) was heated at reflux under nitrogen for 1 hour. The reaction mixture was cooled to r.t. and filtered. The filtrate was concentrated and the residue was chromatographed over silica gel (dichloromethane/hexanes, 80/20) to give 0.65 g (60%) of the desired compound as a pale yellow solid. m.p. 65°-67° C.

Workup

  1. temperatureat reflux under nitrogen for 1 hour
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was chromatographed over silica gel (dichloromethane/hexanes, 80/20)

Sources & evidence

ORD record
ord-6f01fcf8372e4730ae0a24dd46f96661
Source dataset
uspto-grants-1998_01
Patent number
US05708032

Reaction notes

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