Phosphorus pentachloride → HCID 68296403, compound

Reaction equation

[C:1]1([S:7]([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[C:12]=2[C:21]([NH2:23])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:21]([C:12]1[C:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=2[CH:19]=[CH:20][C:11]=1[NH:10][S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:8])=[O:9])#[N:23]

Participants

Procedure

2-Benzenesulfonylamino-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid amide (Intermediate 2, 1.2 g) was dissolved in dry DCM (20 mL) and phosphorous pentachloride (0.9 g) was added. The mixture was stirred for 3 hours then saturated aqueous sodium hydrogencarbonate was added carefully and the products were extracted into ethyl acetate. The organic solution was dried with magnesium sulfate, filtered and the solvent was removed by evaporation. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane. The fractions containing the desired product were combined and the solvent was evaporated to give the title compound as an off-white solid.