Phosphorus sulfide (P2S5) → HCID 23289187, compound

HRID 366336Notes

Reaction equation

HRID 366336 reaction equation
[C:1]([C:4]1[C:8]2[C:9]([Cl:27])=[CH:10][C:11]([F:26])=[C:12]([N:13]3[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]3=[O:25])[C:7]=2[O:6][C:5]=1[CH3:28])(=O)[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:30]>C1(C)C=CC=CC=1>[Cl:27][C:9]1[C:8]2[C:4]([C:1](=[S:30])[CH3:2])=[C:5]([CH3:28])[O:6][C:7]=2[C:12]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]2=[O:25])=[C:11]([F:26])[CH:10]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 15477254HCID 15477254, compound

Product 1

HCID 23289187HCID 23289187, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

100 ml of toluene was added to 0.50 g (1.2 mmol) of 3-(3-acetyl-4-chloro-6-fluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 1.5 g (6.7 mmol) of phosphorus pentasulfide, followed by stirring for 2 hours under heating and refluxing. After completion of the reaction, 100 ml of toluene was further added to the reaction solution. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 47 mg (yield: 9%) of the desired product as an orange colored glassy substance. Refractive index: 1.5967 (20° C.).

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. additionwas further added to the reaction solution
  4. washThe organic layer was washed sequentially with water
  5. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5a89b74fe1cf49c0adbd95378477ade4
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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