Carbon Disulfide → HCID 178505651, compound

HRID 1890945Notes

Reaction equation

HRID 1890945 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[N:12][C:11]([NH:14][NH2:15])=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].[C:18](=S)=[S:19]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([C:18]([SH:19])=[N:15][N:14]=3)[N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 68975343HCID 68975343, compound

Product 1

HCID 178505651HCID 178505651, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of [6-(3-fluoro-phenyl)-[1,2,4]triazin-3-yl]-hydrazine (400 mg, 0.789 mmol) in ethanol (12 mL) was added 2 N aqueous potassium hydroxide (1 mL) followed by carbon disulfide (1 mL). The reaction mixture was stirred at reflux for 1 h, then cooled to room temperature and concentrated in vacuo. The residue was dissolved with 1 N aqueous potassium hydroxide, heated and sonicated then the insolubles were filtered. The filtrate was acidified to pH 2-3 with 1 N aqueous HCl. The resulting precipitate was filtered, washed with water, and dried in vacuo to return title compound as an orange solid (242 mg, 50% yield): 1H NMR (DMSO-d6): δ 7.52 (dt, 1H), 7.70 (dt, 1H), 7.97-8.04 (m, 2H), 9.36 (s, 1H), 14.05 (s, 1H); MS (m/z) 248 [M+H+]+.

Workup

  1. temperatureat reflux for 1 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved with 1 N aqueous potassium hydroxide
  4. temperatureheated
  5. customsonicated
  6. filtrationthe insolubles were filtered
  7. filtrationThe resulting precipitate was filtered
  8. washwashed with water
  9. customdried in vacuo

Sources & evidence

ORD record
ord-afbd9e7fa846402c9e6ad533196972f5
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

Loading…