ACS Infectious Diseases
Article
J = 5.63 Hz, 2H), 8.46 (s, 2H), 8.33−8.32 (m, 2H), 7.68 (t, J =
8.92, 2H). 13C NMR (400 MHz, DMSO-d6) δ 164.98, 162.40,
153.57, 146.25, 136.94, 135.95, 133.22, 131.61, 131.57, 117.73,
117.53, 114.22, 101.56, 101.40. HRMS found 352.1111, M+H.
MP = 317−319 °C.
(1.23 g, 8.8 mmol, 2.2 equiv) and 1,3-diaminoguanidine
hydrochloride (500 g, 4 mmol, 1 equiv) in ethanol (5 mL) was
refluxed for 16 h. Diethyl ether (10 mL) was added, and the
product carbonimidic dihydrazide crashed out of solution as a
white solid. The product was filtered, washed with diethyl
ether, and recrystallized from methanol as a hydrochloride salt.
Yield: 1.48 g, 100%. 1H NMR (400 MHz, DMSO-d6) δ 12.39
(s, 2H), 8.69 (s, 2H), 8.43 (s, 2H), 8.17 (s, 2H), 7.83 (d, J =
6.49 Hz, 2H), 7.59−7.50 (m, 2H). 13C NMR (400 MHz,
DMSO-d6) δ 153.40, 147.93, 135.91, 134.27, 131.11. 130.92,
127.71, 127.06. HRMS found 334.0619, M+H. MP = 268−270
°C.
7: 2,2′-Bis[(2-bromophenyl)methylene]carbonimidic Di-
hydrazide Hydrochloride. A solution of 2-bromobenzaldehyde
(1.23 g, 8.8 mmol, 2.2 equiv) and 1,3-diaminoguanidine
hydrochloride (500 g, 4 mmol, 1 equiv) in ethanol (5 mL) was
refluxed for 16 h. Diethyl ether (10 mL) was added, and the
product carbonimidic dihydrazide crashed out of solution as a
white solid. The product was filtered, washed with diethyl
ether, and recrystallized from methanol as a hydrochloride salt.
Yield: 1.83 g, 100%. 1H NMR (400 MHz, DMSO-d6) δ 12.52
(s, 2H), 8.80 (s, 2H), 8.66 (s, 2H), 8.39 (d, J = 7.64 Hz, 2H),
7.73 (d, J = 7.94, 2H), 7.51 (t, J = 7.43 Hz, 2H), 7.43 (t, J =
7.56, 2H). 13C NMR (400 MHz, DMSO-d6) δ 153.21, 133.66,
133.00, 132.53, 128.87, 128.44, 124.44. HRMS found
423.9586, M+H. MP = 279−281 °C.
2: 2,2′-Bis[(2-fluorophenyl)methylene]carbonimidic Dihy-
drazide Hydrochloride. A solution of 2-fluorobenzaldehyde
(1.1 g, 8.8 mmol, 2.2 equiv) and 1,3-diaminoguanidine
hydrochloride (500 mg, 4 mmol, 1 equiv) in ethanol (5 mL)
was refluxed for 16 h. Diethyl ether (10 mL) was added, and
the product carbonimidic dihydrazide crashed out of solution
as a white solid. The product was filtered, washed with diethyl
ether, and recrystallized from methanol as a hydrochloride salt.
1
Yield: 1.34 g, 99%. H NMR (400 MHz, DMSO-d6) δ 12.54
(s, 2H), 8.72 (s, 2H), 8.64 (s, 2H), 8.36 (dt, J = 7.9, 1.72, 2H),
7.59−7.53 (m, 2H), 7.34 (t, J = 7.9 Hz, 4H). 13C NMR (400
MHz, DMSO-d6) δ 162.21, 159.71, 152.74, 141.62, 132.93,
127.31, 124.75, 120.82, 116.07, 115.86. HRMS found
302.1206, M+H. MP = 293−295 °C.
3: 2,2′-Bis[(3-fluorophenyl)methylene]carbonimidic Dihy-
drazide Hydrochloride. A solution of 3-fluorobenzaldehyde
(1.09 g, 8.8 mmol, 2.2 equiv) and 1,3-diaminoguanidine
hydrochloride (500 mg, 4 mmol, 1 equiv) in ethanol (5 mL)
was refluxed for 16 h. Diethyl ether (10 mL) was added, and
the product carbonimidic dihydrazide crashed out of solution
as a white solid. The product was filtered, washed with diethyl
ether, and recrystallized from methanol as a hydrochloride salt.
8: 2,2′-Bis[(3-bromophenyl)methylene]carbonimidic Di-
hydrazide Hydrochloride. A solution of 3-bromobenzaldehyde
(1.63 g, 8.8 mmol, 2.2 equiv) and 1,3-diaminoguanidine
hydrochloride (500 mg, 4 mmol, 1 equiv) in ethanol (5 mL)
was refluxed for 16 h. Diethyl ether (10 mL) was added, and
the product carbonimidic dihydrazide crashed out of solution
as a white solid. The product was filtered, washed with diethyl
ether, and recrystallized from methanol as a hydrochloride salt.
1
Yield: 1.31 g, 97%. H NMR (400 MHz, DMSO-d6) δ 12.56
(s, 2H), 8.69 (s, 2H), 8.48 (s, 2H), 7.98 (d, J = 10.3 Hz, 2H),
7.70(d, 7.6 Hz, 2H), 7.53 (q, J = 7.3, 2H), 7.33 (t, J = 8.3, 2H).
13C NMR (400 MHz, DMSO-d6) δ 164.14, 161.72, 153.47,
148.02, 136.37, 136.28, 131.34, 131,26, 125.37, 118.15, 117.94,
113.89, 113.66. HRMS found 302.1206, M+H. MP = 281−283
°C.
1
Yield: 1.80 g, 98%. H NMR (400 MHz, DMSO-d6) δ 12.28
4: 2,2′-Bis[(4-fluorophenyl)methylene]carbonimidic Dihy-
drazide Hydrochloride. A solution of 4-fluorobenzaldehyde
(1.09 g, 8.8 mmol, 2.2 equiv) and 1,3-diaminoguanidine
hydrochloride (500 mg, 4 mmol, 1 equiv) in ethanol (5 mL)
was refluxed for 16 h. Diethyl ether (10 mL) was added, and
the product carbonimidic dihydrazide crashed out of solution
as a white solid. The product was filtered, washed with diethyl
ether, and recrystallized from methanol as a hydrochloride salt.
(s, 2H), 8.66 (s, 2H), 8.39 (s, 2H), 8.29 (t, J = 3.08 Hz, 2H),
7.87 (d, J = 7.80, 2H), 7.68 (dd, J = 8.00, 2.79, 2H), 7.45 (t, J =
7.86, 2H). 13C NMR (400 MHz, DMSO-d6) δ 136.13, 133.80,
131.34, 129.95, 128.05, 122.83. HRMS found 423.9589, M+H.
MP = 258−260 °C.
9: 2,2′-Bis[(4-bromophenyl)methylene]carbonimidic Di-
hydrazide Hydrochloride. A solution of 4-bromobenzaldehyde
(1.63 g, 8.8 mmol, 2.2 equiv) and 1,3-diaminoguanidine
hydrochloride (500 g, 4 mmol, 1 equiv) in ethanol (5 mL) was
refluxed for 16 h. Diethyl ether (10 mL) was added, and the
product carbonimidic dihydrazide crashed out of solution as a
white solid. The product was filtered, washed with diethyl
ether, and recrystallized from methanol as a hydrochloride salt.
1
Yield: 1.33 g, 99%. H NMR (400 MHz, DMSO-d6) δ 12.32
(s, 2H), 8.56 (s, 2H), 8.44 (s, 2H), 8.03 (t, J = 6.5 Hz, 4H),
7.34 (t, J = 8.2, 4H). 13C NMR (400 MHz, DMSO-d6) δ
165.24, 162.77, 153.41, 148.14, 130.71, 130.62, 130.48, 130.45,
116.40, 116.19. HRMS found 302.1205, M+H. MP = 295−297
°C.
1
Yield: 1.73 g, 94%. H NMR (400 MHz, DMSO-d6) δ 12.32
5: 2,2′-Bis[(2-chlorophenyl)methylene]carbonimidic Dihy-
drazide Hydrochloride. A solution of 2-chlorobenzaldehyde
(1.23 g, 8.8 mmol, 2.2 equiv) and 1,3-diaminoguanidine
hydrochloride (500 g, 4 mmol, 1 equiv) in ethanol (5 mL) was
refluxed for 16 h. Diethyl ether (10 mL) was added, and the
product carbonimidic dihydrazide crashed out of solution as a
white solid. The product was filtered, washed with diethyl
ether, and recrystallized from methanol as a hydrochloride salt.
(s, 2H), 8.61 (s, 2H), 8.41 (s, 2H), 7.91 (d, J = 8.24 Hz, 4H),
7.70 (d, J = 8.21, 4H). 13C NMR (400 MHz, DMSO-d6) δ
153.32, 148.29, 133.05, 132.23, 130.23, 124.70. HRMS found
423.9587, M+H. MP = 295−297 °C.
10: 2,2′-Bis[(4-methylphenyl)methylene]carbonimidic Di-
hydrazide Hydrochloride. A solution of 4-methylbenzalde-
hyde (1.06 g, 8.8 mmol, 2.2 equiv) and 1,3-diaminoguanidine
hydrochloride (500 mg, 4 mmol, 1 equiv) in ethanol (5 mL)
was refluxed for 16 h. Diethyl ether (10 mL) was added, and
the product carbonimidic dihydrazide crashed out of solution
as a white solid. The product was filtered, washed with diethyl
ether, and recrystallized from methanol as a hydrochloride salt.
1
Yield: 1.42 g, 96%. H NMR (400 MHz, DMSO-d6) δ 12.62
(s, 2H), 8.88 (s, 2H), 8.69 (s, 2H), 8.43 (d, J = 7.15 Hz, 2H),
7.58−7.46 (m, 6H). 13C NMR (400 MHz, DMSO-d6) δ
153.19, 145.53, 134.06, 132.77, 131.03, 130.39, 128.51, 127.95.
HRMS found 334.0620, M+H. MP = 295−297 °C.
6: 2,2′-Bis[(3-chlorophenyl)methylene]carbonimidic Dihy-
drazide Hydrochloride. A solution of 3-chlorobenzaldehyde
1
Yield: 1.11 g, 84%. H NMR (400 MHz, DMSO-d6) δ 12.18
(s, 2H), 8.46 (s, 2H), 8.39 (s, 2H), 7.83 (d, J = 7.8 Hz, 4H),
G
ACS Infect. Dis. XXXX, XXX, XXX−XXX