Phosphorus sulfide (P2S5) → HCID 22041438, compound

HRID 748494Notes

Reaction equation

HRID 748494 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]2[S:6][C:7]([S:10]([NH:13][C:14]3[CH:26]=[CH:25][C:17]([C:18]([NH:20][CH2:21][C:22](=O)[CH3:23])=O)=[CH:16][C:15]=3[S:27]([CH3:30])(=[O:29])=[O:28])(=[O:12])=[O:11])=[C:8]([CH3:9])[C:4]=2[CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:34]>O1CCOCC1>[F:1][C:2]1[CH:32]=[CH:31][C:5]2[S:6][C:7]([S:10]([NH:13][C:14]3[CH:26]=[CH:25][C:17]([C:18]4[S:34][C:22]([CH3:23])=[CH:21][N:20]=4)=[CH:16][C:15]=3[S:27]([CH3:30])(=[O:29])=[O:28])(=[O:12])=[O:11])=[C:8]([CH3:9])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 22041454HCID 22041454, compound

Product 1

HCID 22041438HCID 22041438, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into 5 mL of 1,4-dioxane solution of 150 mg of 4-(5-fluoro-3-methylbenzo[b]thiophene-2-yl)sulfonamido-3-methanesulfonyl-N-(2-oxopropyl)benzamide was added 135 mg of diphosphorus pentasulfide, followed by 4.5 hours of heating under refluxing. The reaction was terminated by adding water to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, successively and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1 to 1/1) to obtain 115 mg of the title compound as amorphous.

Workup

  1. temperatureof heating
  2. temperatureunder refluxing
  3. customThe reaction was terminated
  4. additionby adding water to the reaction mixture
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialsuccessively and then dried over anhydrous sodium sulfate
  8. customThe solvent was removed by evaporation under reduced pressure
  9. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1 to 1/1)

Sources & evidence

ORD record
ord-d367250ffad44e4d9d302c20bad8c185
Source dataset
uspto-grants-2008_07
Patent number
US07399781B2

Reaction notes

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