Cyanamide → HCID 25139615, compound

Temperature

60 °C

A mixture of 8-nitroaniline 254 (510 mg, 2.5 mmol) and cyanamide (460 mg, 10.9 mmol) was melted at 100° C. The mixture was cooled to 60° C. and cHCl (4 mL) was added slowly. The solution was heated at 100° C. for 1 h, then three more aliquots of cyanamide (460 mg, 10.9 mmol) and cHCl (5 mL) were added over 3 h. The solution was cooled to 60° C. and the solution made basic with NaOH solution (7.5 M, 10 mL). The solution was heated at 100° C. for another 1 h, cooled and diluted with water (50 mL). The solid was filtered and washed with water (30 mL) to give 1-oxide 262 (360 mg, 63%) as a brown solid: mp 226-229° C.; 1H NMR [(CD3)2SO] δ 7.50 (d, J=8.6 Hz, 1H, H-5), 7.32 (d, J=8.6 Hz, 1H, H-6), 7.09 (br s, 2H, NH2), 4.09 (s, 2H, H-10), 2.88 (t, J=5.7 Hz, 2H, H-7), 2.58 (t, J=5.7 Hz, 2H, H-8), 2.40 (s, 3H, NCH3); MS (APCI) m/z 232 (MH+, 100%). Anal. calcd for C11H13N5O.¼CH3OH: C, 56.5; H, 5.9; N, 29.3. Found: C, 56.6; H, 5.6; N, 29.1%.

1. temperatureThe solution was heated at 100° C. for 1 h
2. temperatureThe solution was cooled to 60° C.
3. temperatureThe solution was heated at 100° C. for another 1 h
4. temperaturecooled
5. filtrationThe solid was filtered
6. washwashed with water (30 mL)

ORD record

ord-b51f5a1eeeda4961a79288c8d6632a3e

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989451B2