Cyanamide → HCID 25140915, compound

HRID 1669150Notes

Reaction equation

HRID 1669150 reaction equation
[N+:1]([C:4]1[C:5]([NH2:13])=[CH:6][C:7]2[O:11][CH2:10][CH2:9][C:8]=2[CH:12]=1)([O-])=[O:2].[N:14]#[C:15][NH2:16].[CH]Cl.[OH-].[Na+]>O>[N+:1]1([O-:2])[C:4]2[CH:12]=[C:8]3[CH2:9][CH2:10][O:11][C:7]3=[CH:6][C:5]=2[N:13]=[C:15]([NH2:16])[N:14]=1

Participants

6

Reactant 4

HCID 9864CyanamideHCID 14798Sodium HydroxideHCID 6432229CID 6432229HCID 25139753911300-53-3

Product 1

HCID 25140915HCID 25140915, compoundYield 189.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of nitroaniline 203 (4.0 g, 22.2 mmol) and cyanamide (7.2 g, 171 mmol) were mixed together at 80° C., cooled to 50° C., cHCl (8.0 mL) added carefully and the mixture heated at 80° C. for 4 h. 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 (20 mL), filtered, washed with water (20 mL) and ether (5 mL), and dried to give 1-oxide 204 (8.6 g, 96%) as a yellow powder: mp (DCM) 293-296° C.; 1H NMR [(CD3)2SO] δ 7.71 (s, 1H, H-9), 6.23 (s, 1H, H-5), 4.59 (t, J=8.5 Hz, 2H, H-7), 3.12 (t, J=8.5 Hz, 2H, H-8), NH2 not observed; HRMS (FAB+) calcd for C9H9N4O2 (MH+) m/z 205.0726, found 205.0725.

Workup

  1. additionwere mixed together at 80° C.
  2. temperaturethe mixture heated at 80° C. for 4 h
  3. temperatureThe mixture was cooled to 50° C.
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. washwashed with water (20 mL) and ether (5 mL)
  7. customdried

Sources & evidence

ORD record
ord-faa7d5ebfe234c45a2fcde171eb90c94
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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