N,N-Dimethyl-1,3-propanediamine → HCID 19605482, compound
Reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[C:4]([Br:18])[N:3]=1.[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][CH2:23][NH2:24]>O1CCOCC1>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([S:8]([C:6]2[CH:5]=[C:4]([Br:18])[N:3]=[C:2]([NH:24][CH2:23][CH2:22][CH2:21][N:20]([CH3:25])[CH3:19])[CH:7]=2)(=[O:10])=[O:9])=[CH:12][CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
0.16 g (0.00041 mol) of 4-(2,6-dibromopyridine-4-sulphonyl)-phenylamine was dissolved in 6 ml of dioxane and treated with 0.52 ml of 3-dimethylamino-1propylamine. The mixture was stirred at 60° C. for 24 hrs., the solvent was removed and the residue was chromatographed on silica gel firstly with 5% methanol in dichloromethane and then with 10% methanol in dichloromethane. The product-containing fractions were freed from solvent, the residue was dissolved in 1N HCl, filtered and the filtrate was adjusted to pH 9 with 1N NaOH. The precipitate which thereby resulted was filtered off under suction and dried in a high vacuum. There was obtained 0.072 g (43%) of N-[4-(4-aminobenzenesulphonyl)-6-bromopyridin-2-yl]-N',N'-dimethylpropane-1,3-diamine as pink coloured crystals; m.p.: >250° C. (dec.).