Cyanamide → HCID 25139024, compound

HRID 1669185Notes

Reaction equation

[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([NH2:15])=[C:7]([N+:12]([O-:14])=O)[CH:8]=2)[CH2:3]1.[N:16]#[C:17][NH2:18].[CH]Cl.[OH-].[Na+]>O>[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[CH:8]=[C:7]3[N+:12]([O-:14])=[N:16][C:17]([NH2:18])=[N:15][C:6]3=[CH:5][C:4]=2[CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 6-nitroaniline 255 (2.3 g, 10.7 mmol) and cyanamide (2.0 g, 46.6 mmol) was melted at 100° C. The mixture was cooled to 60° C. and cHCl (5 mL) was slowly added. The solution was heated at 100° C. for 90 min, then a further three aliquots of cyanamide (2.1 g) and cHCl (5 mL) were added over 3 h. The solution was cooled to 50° C. and made basic with NaOH solution (7.5 M, 20 mL). The solution was heated at 100° C. for another 90 min, cooled and diluted with water (50 mL). The solid was filtered and washed with water to give 1-oxide 256 (1.70 g, 66%) as a brown solid: mp 170-175° C.; 1H NMR [(CD3)2SO] δ 7.90 (s, 1H, H-10), 7.25 (s, 1H, H-5), 7.15 (br s, 2H, NH2), 3.62 (s, 2H, H-6), 2.96 (t, J=5.9 Hz, 2H, H-8), 2.62 (t, J=5.9 Hz, 2H, H-9), 2.35 (s, 3H, NCH3); 13C NMR δ 159.8, 146.8, 144.3, 132.0, 128.4, 121.9, 118.3, 57.3, 51.9, 45.4, 28.3; MS (APCI) m/z 232 (MH+, 100%). Anal. calcd for C11H13N5O.½H2O: C, 55.0; H, 5.9; N, 29.1. Found: C, 55.6; H, 5.5; N, 28.7%.

Workup

temperatureThe solution was heated at 100° C. for 90 min
temperatureThe solution was cooled to 50° C.
temperatureThe solution was heated at 100° C. for another 90 min
temperaturecooled
filtrationThe solid was filtered
washwashed with water

Sources & evidence

ORD record: ord-e676e7543d5b4914b6b3cbcad368b5dc
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989451B2

Reaction notes

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