Hydrochloric Acid → HCID 178426711, compound

Temperature

80 °C

20 g of 2-Methyl-5-nitroaniline (0.131 mol; 1 eq.), 11.05 g of cyanamide (0.263 mol; 2 eq.) and 80 mL of isopropyl alcohol were placed in a reactor flask. The reaction mixture was heated to 80° C., and 18 mL of concentrated hydrochloric acid was slowly added dropwise within 80 minutes. The reaction mixture was stirred for 1 hour while maintaining the temperature at 80° C. Next, 6 mL of concentrated hydrochloric acid was added dropwise and the reaction mixture was kept at 80° C. for 2 hours. The reaction mixture was cooled down to 60° C. and 10 mL of 65% nitric acid (0.142 mol, 1.08 eq.) was added dropwise and the mixture was left with stirring until it was cooled down to room temperature. The solid product was filtered off, washed with 50 mL of isopropyl alcohol and dried in the air to afford 27.45 g (yield 81.1%) of 1-(2-methyl-5-nitrophenyl)guanidine nitrate, m.p. 203-206° C.; 1H NMR (DMSO-d6, 200 MHz): 2.32 (3H, s, CH3), 7.44 (4H, m, 4×NH), 7.64 (1H, d, J=8.2 Hz, 3-H), 8.09 (1H, d, J=2.5 Hz, 6-H), 8.15 (1H, dd, J=8.2 i 2.5 Hz, 4-H), 9.51 (1H, m, NH+).

1. temperaturewhile maintaining the temperature at 80° C
2. waitthe reaction mixture was kept at 80° C. for 2 hours
3. temperatureThe reaction mixture was cooled down to 60° C.
4. waitthe mixture was left
5. stirringwith stirring until it
6. temperaturewas cooled down to room temperature
7. filtrationThe solid product was filtered off
8. washwashed with 50 mL of isopropyl alcohol
9. customdried in the air

ORD record

ord-489ca6f9502c4e34a108d3c158d4d7c2

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07674901B2