Benzyl Bromide → 2-(Benzyloxycarbonyl)-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

반응식

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]([NH:12][S:13]([C:16]2[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=2[C:18]([OH:20])=[O:19])(=[O:15])=[O:14])=[O:11])[N:3]=1.C(N(CC)CC)C.[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1>[CH2:32]([O:19][C:18]([C:17]1[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=1[S:13]([NH:12][C:10]([NH:9][C:4]1[N:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[N:3]=1)=[O:11])(=[O:15])=[O:14])=[O:20])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

참가 물질

실험 절차

To 1.75 g of 2-(4,6-dimethylpyrimidin-2-ylaminocarbonylsulfamoyl)benzoic acid was added 0.51 g of triethylamine in 10 ml tetrahydrofuran and 0.88 g of benzyl bromide in 10 ml of tetrahydrofuran. The mixture was heated to reflux for 1.5 hours, filtered and the tetrahydrofuran evaporated in-vacuo. The residue was extracted with hot 1-chlorobutane, diluted with ethyl acetate, washed with water and saturated aqueous sodium bicarbonate. The organic phase was dried over magnesium sulfate, filtered and the solvents evaporated in-vacuo. The resultant residue was crystallized from 1-chlorobutane to a melting point of 157°. This product showed absorption peaks in the infrared region at 1720, 1600, 1560 cm-1 consistent for the desired ester and absorption by nuclear magnetic resonance at 2.45', singlet, for CH3 ; 5.3δ singlet, CH2 on benzyl; 6.65' singlet CH of pyrimidine and aryl peaks at 7-8δ.