Sodium → HCID 178448644, compound

Participants

Reaction Conditions

Reaction Steps

N-[(5-Bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine and N-[(6-bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine are prepared as described in Example 9, starting with 30 cm3 of absolute ethanol, 0.36 g of sodium, 1.5 g of guanidinium chloride and 3.7 g of ethyl (5-bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate and ethyl (6-bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate in 20 cm3 of absolute ethanol. The reaction mixture is stirred at a temperature in the region of 20° C. for 16 hours and is then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is taken up in a mixture of 100 cm3 of water and 200 cm3 of ethyl acetate. The organic phase is washed with 100 cm3 of water and then with 150 cm3 of saturated sodium chloride solution. This organic phase is dried over magnesium sulfate and concentrated under reduced pressure (2 kPa) at a temperature in the region of 40° C. A white solid is thus obtained, which is then taken up again and stirred in a mixture of 15 cm3 of water and 50 cm3 of diethyl ether for 1.5 hours at a temperature in the region of 20° C. The white solid thus obtained is filtered off, washed with twice 50 cm3 of diethyl ether and dried in a desiccator under reduced pressure (2 Pa) at a temperature in the region of 35° C. 0.92 g of N-[(5-bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine and N-[(6-bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine are thus obtained in the form of a white powder. (Analysis: C15 H19 Br N4 O2, % calculated C, 49.06; H, 5.21; Br, 21.76; N, 15.26; O, 8.71%. found C, 48.97; H, 5.34; Cl, 14.72; N, 21.52). Mass spectrum: EI: m/e 366 (M+), m/e 279, m/e 86 (base peak).

Provenance & Evidence