REACTION OF CYANAMIDES WITH N,N-BINUCLEOPHILES
1651
Table 2. (Contd.)
Comp.
no.
Chemical shifts , ppm
XId
XId
XIe
2.42 s (6H, 2CH3), 3.79 t (2H, CH2), 4.02 t (2H, CH2), 6.76 s (H, CHpyrim), 7.29 d (2H, arom.), 7.60 d (2H,
arom.), 9.42 s (H, NH), 13.02 s (H, NH)
2.45 s (6H, 2CH3), 3.69 t (2H, CH2), 4.24 t (2H, CH2), 6.83 s (1H, CHpyrim), 7.21 7.38 m (3H, arom.), 7.63
7.78 m (2H, arom.), 9.84 s (1H, NH), 14.76 s (1H, NH)
2.25 s (3H, CH3 arom.), 2.29 s (3H, CH3 arom.), 2.45 s (6H, 2CH3pyrim), 3.71 t (2H, CH2), 4.32 t (2H, CH2),
6.70 s (1H, CHpyrim), 7.08 d (1H, arom.), 7.47 m (2H, arom.), 9.61 s (1H, NH), 15.09 s (1H, NH)
1.3 2.3 m (7H, aliph.), 2.44 s (6H, 2CH3), 2.9 3.5 m (3H, aliph.), 6.82 s (1H, CHpyrim), 7.05 7.17 m (1H, arom.),
XIIa
XIIb
7.38 m (2H, arom.), 7.58 d (2H, arom.), 9.32 s (1H, NHguanid.), 13.02 s (1H, NHamid
1.32 2.34 m (7H, aliph.), 2.45 s (6H, 2CH3), 2.9 3.4 m (3H, aliph.), 6.88 s (1H, CHpyrim), 7.48 d (1H, arom.),
7.74 d (1H, arom.), 8.26 s (1H, arom.), 9.53 s (1H, NHguanid.), 12.96 s (1H, NHamid
)
)
XIIIa 2.05 s (6H, 2CH3), 4.02 s (4H, CH2CH2), 6.47 s (1H, CHpyrim), 7.28 7.59 m (10H, arom.)
XIIIb 2.08 s (6H, 2CH3), 3.80 s (6H, 2OCH3), 4.05 s (4H, CH2CH2), 6.35 s (1H, CHpyrim), 6.83 d (4H, arom.), 7.57 d
(4H, arom.)
XVa
XVb
XVc
2.45 s (6H, 2CH3), 6.95 d (2H, naphth.), 7.12 s (1H, CHpyrim), 7.35 7.53 m (4H, naphth.), 12.35 br.s.(2H, 2NH)
6.74 d (2H, naphth.), 7.11 7.28 m (4H, naphth.), 7.53 7.68 m (5H, arom.), 11.86 br.s. (2H, 2NH)
6.71 d (2H, naphth.), 7.11 7.28 m (4H, naphth.), 7.41 d (2H, arom.), 8.18 d (2H, arom.), 11.71 br.s. (2H, 2NH)
heated for 8 h under After cooling, the precipitate was
filtered off and recrystallized from dioxane. Mass
spectrum, m/z (Irel, %): 191 (80), 190 (100), 162 (19),
149 (7), 134 (26), 123 (24), 108 (48), 93 (7), 67 (19),
55 (8), 42 (20).
N-(1,3-Dibenzyltetrahydro-1H-imidazol-2-ylidene)-
4,6-dimethylpyrimidin-2-amine (IX). A mixture of
1.48 g of cyanamide I and 2.88 g of N,N -dibenzyl-
ethylenediamine (VIII) in 15 ml of dioxane was
heated for 10 h under reflux. After cooling, the pre-
cipitate was filtered off and recrystallized from
dioxane.
2-(4,6-Dimethylpyrimidin-2-ylamino)-N-phenyl-
4,5-dihydro-1H-imidazole-1-carboxamide (XIb).
Compound VI, 1.91 g, was dissolved in 10 ml of an-
hydrous N,N-dimethylacetamide (DMA) on heating,
1.09 ml of phenyl isocyanate was added, and the
mixture was heated for 5 h at 90 C. The precipitate
was filtered off and recrystallized from dioxane DMA.
N-(3-Chlorophenyl)-2-(4,6-dimethylpyrimidin-2-
ylamino)-4,5-dihydro-1H-imidazole-1-carboxamide
(XIc), N-(4-chlorophenyl)-2-(4,6-dimethylpyrimi-
din-2-ylamino)-4,5-dihydro-1H-imidazole-1-carb-
oxamide (XId), 2-(4,6-dimethylpyrimidin-2-yl-
amino)-N-phenyl-4,5-dihydro-1H-imidazole-1-car-
bothioamide (XIe), and N-(3,4-dimethylphenyl)-2-
(4,6-dimethylpyrimidin-2-ylamino)-4,5-dihydro-
1H-imidazole-1-carbothioamide (XIf) were syn-
thesized in a similar way.
4,6-Dimethyl-N-(perhydrobenzimidazol-2-yl-
idene)pyrimidin-2-amine (Xa). A mixture of 1.48 g
of cyanamide I and 1.5 ml of trans-cyclohexane-1,2-
diamine in 15 ml of dioxane was heated for 10 h
under reflux. The mixture was cooled, and the pre-
cipitate was filtered off and recrystallized from di-
oxane.
2-(4,6-Dimethylpyrimidin-2-ylamino)-N-phenyl-
3a,4,5,6,7,7a-hexahydro-1H-benzimidazole-1-car-
boxamide (XIIa). Compound X, 2.45 g, was dis-
solved in 10 ml of anhydrous DMA on heating,
1.09 ml of phenyl isocyanate was added, and the mix-
ture heated for 5 h at 90 C. The precipitate was fil-
tered off and recrystallized from dioxane DMA.
N-(Perhydrobenzimidazol-2-ylidene)benzamide
(Xb) and 4-chloro-N-(perhydrobenzimidazol-2-yl-
idene)benzamide (Xc) were synthesized in a similar
way.
2-(4,6-Dimethylpyrimidin-2-ylamino)-N-ethyl-
4,5-dihydro-1H-imidazole-1-carboxamide (XIa).
Compound VI, 1.91 g, was dissolved in 10 ml of an-
hydrous dioxane on heating, 0.8 ml of ethyl iso-
cyanate was added, and the mixture was heated for 5 h
at 90 C. The resulting solution was evaporated on a
rotary evaporator, and the residue was recrystallized
from 2-propanol.
N-(3,4-Dichlorophenyl)-2-(4,6-dimethylpyri-
midin-2-ylamino)-3a,4,5,6,7,7a-hexahydro-1H-
benzimidazole-1-carboxamide (XIIb) was synthe-
sized in a similar way.
3-Benzoyl-2-(4,6-dimethylpyrimidin-2-ylimino)-
imidazolidin-1-yl(phenyl)methanone (XIIIa). Com-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 76 No. 10 2006