Cyanamide → HCID 25140031, compound

HRID 1669122Notes

Reaction equation

HRID 1669122 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=[O:12])[CH2:7][CH:6]([CH2:14][CH2:15][OH:16])[CH2:5]2.[N:17]#[C:18][NH2:19].[CH]Cl.[OH-].[Na+]>>[NH2:19][C:18]1[N:17]=[N+:11]([O-:12])[C:10]2[CH:9]=[C:8]3[C:4]([CH2:5][CH:6]([CH2:14][CH2:15][OH:16])[CH2:7]3)=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 4

HCID 9864CyanamideHCID 14798Sodium HydroxideHCID 6432229CID 6432229HCID 25139342HCID 25139342, compound

Product 1

HCID 25140031HCID 25140031, compoundYield 94.6%

Conditions

Temperature
100 °C

Procedure

A mixture of nitroaniline 156 (17.6 g, 79 mmol) and cyanamide (19.8 g, 471 mmol) were melted together at 60° C. and cHCl (35 mL) was added dropwise. The solution was heated to 100° C., stirred for 1 h, cooled to ca. 50° C. and the mixture made strongly basic with 7.5 M NaOH solution. The mixture was heated to 100° C. for 3 h, cooled to 20° C. and diluted with ice/water. The resulting precipitate was filtered, washed with H2O (100 mL) and Et2O (30 mL), and dried to give 1-oxide 157 (18.4 g, 94%) as a yellow-green solid: mp 230-235° C.; 1H NMR [(CD3)2SO] δ 7.92 (s, 1H, H-9), 7.33 (s, 1H, H-5), 7.11 (br s, 2H, NH2), 4.45 (br s, 1H, OH), 3.49 (t, J=6.6 Hz, 2H, CH2O), 3.06-3.15 (m, 2H, H-6, H-8), 2.59-2.69 (m, 2H, H-6, H-8), 2.49-2.54 (m, 1H, H-7), 1.63 (q, J=6.6 Hz, 2H, CH2); HRMS calcd for C12H14N4O2 (M+) m/z 246.1117, found 246.1115.

Workup

  1. customwere melted together at 60° C.
  2. temperaturecooled to ca. 50° C.
  3. temperatureThe mixture was heated to 100° C. for 3 h
  4. temperaturecooled to 20° C.
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with H2O (100 mL) and Et2O (30 mL)
  7. customdried

Sources & evidence

ORD record
ord-00046880e31048c1af3384dcccd1351e
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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