Methanol → HCID 454853、化合物

反応式

C(OO)(=O)[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)C(O)=O.[Mg].[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:25]([NH2:27])=S)=[C:19]2C1C=CC=CC=1.[S:34]([O-])([O-])(=[O:36])=S.[Na+].[Na+].C[OH:42]>>[Cl:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([C:25]([NH2:27])=[O:42])=[C:19]2[S:34]([C:2]1[CH:3]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:36]

参加物

反応物 4

HCID 887Methanol2 回

HCID 24477Sodium Thiosulfate

HCID 9815656Magnesium monoperoxyphthalic acid

HCID 14567454HCID 14567454、化合物

生成物 1

HCID 454853HCID 454853、化合物

反応条件

温度: 20 °C

実験手順

A solution of magnesium monoperoxyphthalic acid (85% peracid) (11.8 mg, 0.024 mmol) in methanol (2 mL) was added dropwise to a solution of 5-chloro-3-phenylthioindole-2-carboxamide (14.5 mg, 0.048 mmol) in methanol (2 mL) at 0° C. The reaction was stirred at 20° C. for 4 hours. A solution of 10% aqueous sodium thiosulfate was added and the reaction stirred vigorously for 10 minutes. Methanol was removed in vacuo and the residue partitioned between ethyl acetate and water. The ethyl acetate extract was washed with brine and dried over magnesium sulfate. The crude product was purified by column chromatography on silica gel with 30-40% ethyl acetate in hexane. The title compound was obtained as a white solid. NMR, (DMSO-d6, 300 MHz) δ12.53(1H, s), 8.35(1H,br s), 8.08(1H,br s), 7.83(1H,d,J=2 Hz), 7.71(2H,d,J=8 Hz), 7.52(4H,m), 7.30(1H,dd,J=9,2 Hz).