Butyl isocyanate → N-(Butylaminocarbonyl)-2-chloro-6-phenylbenzenesulfonamide

反応式

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[S:14]([NH2:17])(=[O:16])=[O:15].[CH2:18]([N:22]=[C:23]=[O:24])[CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:18]([NH:22][C:23]([NH:17][S:14]([C:3]1[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:16])=[O:15])=[O:24])[CH2:19][CH2:20][CH3:21]

参加物

実験手順

A mixture of 7.7 g (0.029 mol) 2-chloro-6-phenylbenzenesulfonamide, 3.6 ml (0.032 mol) n-butylisocyanate and 4.1 g (0.03 mol) potassium carbonate was heated in 80 ml dry acetonitrile for 18 hours at reflux. The solvent was evaporated and the residue treated with 1N HCl and ethyl acetate and the insoluble solids were collected, washed with water and then ether. Additional material was obtained from the organic phase of the filtrate to afford a total of 10 g of the title compound, m.p. 184°-186°. NMR (90 MHz, CDCl3), 0.9 (CH3, t, br), 1.4 (4H, m), 3.05 (q, J=7 Hz, 2H), 5.9 (t, br, NH), 7.2-7.6 (m, 8H) ppm.