Cyanamide → HCID 11952004, compound

Temperature

100 °C

A mixture of nitroaniline 93 (3.0 g, 15.7 mmol) and cyanamide (2.6 g, 62.6 mmol) was mixed together at 80° C., cHCl (5 mL) added dropwise and the mixture heated at 100° C. for 3 h. A further three aliquots of cyanamide (0.5 g, 11.9 mmol) and cHCl (0.5 mL) were added over two hours. The mixture was cooled to 50° C., 7.5 M NaOH solution added until the mixture was strongly basic and the mixture stirred at 100° C. for 3 h. The mixture was cooled, diluted with water (100 mL), filtered, washed with water (2×30 mL), and dried. The residue was purified by chromatography, eluting with a gradient (0-15%) of MeOH/DCM, to give 1-oxide 94 (3.06 g, 90%) as a yellow powder: mp (MeOH/DCM) 275-277° C.; 1H NMR [(CD3)2SO] δ 7.90 (s, 1H, H-9), 7.31 (s, 1H, H-5), 7.10 (br s, 2H, NH2), 3.05-3.14 (m, 2H, CH2), 2.48-2.62 (m, 3H, H-7, CH2), 1.09 (d, J=6.3 Hz, 3H, CH3); 13C NMR [(CD3)2SO] δ 159.9, 153.7, 148.6, 142.1, 128.7, 120.0, 113.9, 41.4, 39.6, 34.3, 19.9. Anal. calcd for C11H12N4O: C, 61.1; H, 5.6; N, 25.9. Found: C, 61.3; H, 5.6; N, 26.2%.

1. additionwas mixed together at 80° C.
2. temperatureThe mixture was cooled to 50° C.
3. temperatureThe mixture was cooled
4. filtrationfiltered
5. washwashed with water (2×30 mL)
6. customdried
7. customThe residue was purified by chromatography
8. washeluting with a gradient (0-15%) of MeOH/DCM

ORD record

ord-c341c59ecbb446ca9e705dd6e8ea5282

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989451B2