Phosphorus sulfide (P2S5) → HCID 86760613, compound
Reaction equation
C([O-])(O)=O.[Na+].[CH3:6][O:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[NH:16][C:17](=O)[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:27]>COCCOC>[CH3:6][O:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[NH:16][C:17]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[S:27]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
11 g (131 mmol; 4 equivalents) of NaHCO3 is added to 9 g (32.7 mmol) of N-(2,4-dimethoxyphenyl)-4-fluorobenzamide dissolved in 350 ml of 1,2-dimethoxyethane. 29 g (65.2 mmol; 2 equivalents) of phosphorus pentasulphide (P2S5) is then added by parts to the reaction medium which is maintained under stirring under an inert atmosphere of argon at 85° C. for 4 hours. 250 ml of a saturated solution of NaHCO3 are then added to the medium then the product is extracted with 3 times 200 ml of ethyl acetate. The combined organic phases are washed with twice 200 ml of a saturated solution of NaCl, then dried over sodium sulphate. The solvents are evaporated off under reduced pressure and the residue purified on a silica column (eluent: ethyl acetate/heptane mixture 1:4) in order to provide 4.65 g (yield=49%) of expected product.
Workup
- temperatureis maintained
- extractionthe product is extracted with 3 times 200 ml of ethyl acetate
- washThe combined organic phases are washed with twice 200 ml of a saturated solution of NaCl
- dry with materialdried over sodium sulphate
- customThe solvents are evaporated off under reduced pressure
- customthe residue purified on a silica column (eluent: ethyl acetate/heptane mixture 1:4) in order
Sources & evidence
- ORD record
- ord-c0a4d35a7c4e4b08a35ff8cfa6f52836
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07335674B2
Reaction notes
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