Synthesis and Antibacterial Activity Studies of Some 989
Preparation of 2-(4’-methyl phenyl amino)-s-triazine 1
p-Toluidine (0.01 mole) was added slowly to cyanuric chloride (0.01 mole) in dioxane
o
(30 mL) with constant stirring for 4 h at 0 to 5 C. Then sodium carbonate (0.005 mole)
dissolved in water (10 mL) was added drop wise to neutralize HCl evolved during the
reaction. Finally the contents were poured into ice. The solid separated out was
0
filtered, washed with water, dried and recrystallized from alcohol. m.p 196 C, yield
86%.
Preparation of bis-2,4- (4’-methyl phenyl amino)- s-triazine 2
p-Toluidine (0.01 mole) was added slowly to compound I (0.01 mole) in dioxane
(35 mL) with constant stirring for 6 h at room temperature. Then sodium carbonate
(0.005 mole) dissolved in water (10 mL) was added drop wise to neutralize HCl evolved
during the reaction. Finally the contents were poured into crushed ice. The solid
separated out was filterd, washed with water, dried and recrystallized from alcohol.
0
m.p.179 C.yield 80%.
Preparation of bis 2,4-(4’-methyl phenyl amino)–s-triazin-6-yl-aminoethyl benzoate 3
Ethyl p-aminobenzoate (0.01 mole) and compound 2 (0.01 mole) were dissolved in
dioxane (40 mL). The reaction mixture was refluxed for 6 h, cooled and poured into
crushed ice. Then sodium carbonate (0.005 mole) dissolved in water (10 mL) was
added to neutralize HCl evolved during the reaction. The solid separated out was
0
filtered, washed with water, dried and recrystallized from alcohol. m.p. 219 C yield
78%. IR (KBr, cm-1), 2956(C-H),3102(Ar-H), 1470(C=N), 806(C-N) 3362(N-H),
1680(C=O).
Preparation of bis-2,4-(4’-methylphenylamino)-s-triazine-6-ylaminobenzoyl hydrazone 4
A mixture of compound 3(0.01 mole) in dioxane and hydrazine hydrate (0.01 mole), was
refluxed on a water bath for 6 h. The product was isolated with HCl and crystallized from
dioxane.m.p.198 yield 79 IR (KBr, cm-1), 2908(C-H), 3056(Ar-H), 1498(C=N), 807(C-N),
3356(N-H), 1670(C=O).
Preparation of bis-2,4(4’-methylphenylamino)-s-triazine-6-ylaminobenzoyl substituted
benzylhydrazone 5
A mixture of compound 4 (0.01 mole) and substituted aldehyde (0.01 mole) in dioxane
(15 mL) was refluxed for 4hrs. The product was isolated and crystallized from methanol.
0
m.p.150 C.Yield78%. IR (KBr,cm-1) 2985(C-H), 3056(Ar-H), 3399(N-H), 1420 (C= N),
1675(C=O), 805(C-N). 1HNMR (CDCl3 ,), 6.45 (Sym.multi. 2CH3 subs. Benzene ring 8H),
7.68 (S,4N-H,4H), 2.38 (s,2CH3,6H), 1.95(s,C-H of thiazolidinone), 6.31 (sym.multi.N-H
subs.benzene ring)
Preparation of 2-substitutedphenyl-3-bis-2,4-(4’-methylphenylamino)-s-triazine-6-
ylaminobenzoyl amino-5-H-4- thiazolidinone 6
Thioglycolic acid (0.01 mole) was added to compound 5 (0.01 mole) in dry bezene
(20 mL)and refluxed for 6 h. The product was isolated by washing the upper organic layer
0
with water and sodium bicarbonate solution and crystallized from dioxane. m.p. 197 C
yield 76%. IR(max in cm-1),3456(N-H,3095(Ar-H), 1602(C=C), 1675 (C=O), 750(C-S), 1306
(C=N),802(C-N)675(Ar-Cl). 1HNMR(CDCl3, ), 6.40 (sym. multi., 8H,2CH3 subs.benzene ring),
7.45(s,4H,N-H sub. Benzene ring) 2.38(s, 2CH3, 6H).
Ahirwar, Mukesh Kumar
