Phosphorus oxychloride → HCID 9946483, compound

HRID 1244773Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:14][N:15]([C:17]([NH2:19])=[S:18])[NH2:16].O=P(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[CH:5]1([N:19]=[C:17]2[N:15]([CH3:14])[N:16]=[C:9]([C:8]3[CH:12]=[CH:13][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[S:18]2)[CH2:13][CH2:12][CH2:8][CH2:7][CH2:6]1

Participants

Conditions

Temperature: 95 °C

Procedure

To a mixture of 4-methylsulfonyl-benzoic acid (2.5 mmol, 500 mg), 2-methylthiosemicarbazide (5a) (2.5 mmol, 468 mg) in anhydrous dioxane (5 mL) at 65° C., POCl3 (3 mmol, 280 μL) was added, and the mixture was warmed at 95° C. for 5 hours. The solvent was removed by distillation under reduced pressure to give a crude material which was basified at pH 8-7 with a saturated solution of NaHCO3. The aqueous phase was extracted with dichloromethane. The organic layer was washed with saturated solution of NaCl, dried over magnesium sulfate, filtered, and distilled to give a residue which was purified by silica gel chromatography (eluted with a gradient of cyclohexane/ethyl acetate finishing with the ratio 80:20) to afford 230 mg of the title compound. Yield: 26%.

Workup

customThe solvent was removed by distillation under reduced pressure
customto give a crude material which
extractionThe aqueous phase was extracted with dichloromethane
washThe organic layer was washed with saturated solution of NaCl
dry with materialdried over magnesium sulfate
filtrationfiltered
distillationdistilled
customto give a residue which
customwas purified by silica gel chromatography (
washeluted with a gradient of cyclohexane/ethyl acetate finishing with the ratio 80:20)

Sources & evidence

ORD record: ord-b7a537bc1ef4424b8fcc03f7056692cc
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122565B2

Reaction notes

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