Synthesis of 1- (1-adamantyl) -3,4,5-trinitro-1H-pyrazole.
To 1.5 g (0.00739 mol) of 3,4,5-trinitro-1H-pyrazole in 20 ml of diethyl ether at 0 ° C was added dropwise a solution of 1 g (0.00739 mol) of 1,3-svezhevozognannogo dehydroadamantane in 20 ml of diethyl ether. The mixture was kept under stirring for 1 hour at 0 ° C, the temperature was raised why to reflux and held for an additional 3 hours. The solvent was distilled off. The product was purified by recrystallization from ethanol.
Yield 2.44 g (98%). Mp = 139-140 ° C.
Mass spectrum, m / z (intensity,%): 337 (M + , 2%), 292 ([M-NO 2 ] + , 2%), 247 (2%), 245 ([M- (NO 2 ) 2 ] +, 2%), 199 ([M-3NO 2 ] + , 2%), 177 (36%), 151 (21%), 150 (48%), 135 (Ad + , 96%), 121 (48%), 107 (56%) 95 (71%), 93 (100%) 67 (45%) 55 (75%).
NMR 1 H (300 MHz, DMSO-d 6 ), δ, ppm .: 1.66 (6H, CH 2 , H delta -Ad), with 2.1 (3H, CH, H y -Ad), 2.18 to (6H, CH 2 , H beta -Ad).
NMR 13 C (75.47 MHz, CDCl 3 ), δ, ppm .: 71.8872 (s, 1C, C alpha -Ad), 41.0302 (s, 3C, C beta -Ad), 35.2616 (s, 3C, C delta -Ad), 29.9234 (s, 3C, C y -Ad).
A process for production of 1- (1-adamantyl) -3,4,5-trinitro-1H-pyrazole (RU 2528404):
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