Sodium hydride → 1-(6-Chloro-3-pyridylmethyl)-1-formyl-3,3-dimethyl-2-nitroguanidine

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Reaction Steps

To a mixture of 0.26 g of 1-(6-chloro-3-pyridylmethyl)3,3-dimethyl-2-nitroguanidine (Compound No. 6) and 3 ml of dry THF was added 0.08 g of 60% sodium hydride (in mineral oil) in a water bath of 20° C., followed by stirring for 30 minutes. A solution of 0.26 g of acetic formic anhydride in 0.5 ml of THF was added to the reaction mixture in one minute, and then stirred for 12 hours after the bath was removed. After adding 0.5 ml of acetic acid, the reaction mixture was concentrated. The residue was purified by a column chromatography [developing solvent: dichloromethanemethanol (30:1)] to obtain 0.10 g of 1-(6-chloro-3-pyridylmethyl)-1-formyl-3,3-dimethyl-2-nitroguanidine (Compound No. 22) as a syrup. 1H NMR(CDCl3): 3.03(6H,s), 4.70(2H,s), 7.36(1H,d,J=8.7 Hz), 7.74(1H,dd,J=8.7, 2.7 Hz), 8.40(1H,d,J=2.7 Hz), 8.44(1H,s)

Provenance & Evidence