Allyl bromide → 4-(2-fluoro-4-nitrophenyl)tetrahydro-2-(2-propenyl)-2H-1,2-thiazine 1,1-dioxide

反応式

C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[CH:17]1[CH2:22][CH2:21][S:20](=[O:24])(=[O:23])[NH:19][CH2:18]1.[CH2:25](Br)[CH:26]=[CH2:27]>C(#N)C>[F:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[CH:17]1[CH2:22][CH2:21][S:20](=[O:24])(=[O:23])[N:19]([CH2:27][CH:26]=[CH2:25])[CH2:18]1

参加物

実験手順

Anhydrous potassium carbonate (3.6 g, 26.1 mmol) is added to a solution of of 4-(2-fluoro-4-nitrophenyl)tetrahydro-2H-1,2-thiazine 1,1-dioxide (1.795 g, 6.54 mmol) and allyl bromide (2.0 ml, 23.1 mmol) in dry acetonitrile (25 ml). The mixture is heated to reflux for 5 min then cooled. After filtration and evaporation the residue is chromatographed over silica gel (150 g) eluting with 0-1% methanol-chloroform. The title compound is obtained as flakes (1.70 g, 83%) mp 121°.