Carbon Disulfide → HCID 178480034, compound

HRID 1890940Notes

Reaction equation

HRID 1890940 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[N:11][C:10]([NH:13][NH2:14])=[CH:9][CH:8]=2)[CH:4]=[N:3]1.[OH-].[K+].[C:17](=S)=[S:18]>C(O)C.O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:17]([SH:18])=[N:14][N:13]=3)[N:12]=2)[CH:4]=[N:3]1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 58075172HCID 58075172, compound

Product 1

HCID 178480034HCID 178480034, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of [6-(1-methyl-1H-pyrazol-4-yl)-pyridazin-3-yl]-hydrazine (18 g, 94.7 mmol) in ethanol (230 mL) and water (63 mL) was added KOH (5.63 g, 100 mmol), followed by CS2 (12 mL, 198 mmol). The mixture was stirred and heated to reflux for 2 h under nitrogen atmosphere. The mixture was cooled to room temperature and concentrated in vacuo. The residue was dissolved in 1 N aqueous sodium hydroxide and the insolubles were filtered off. The filtrate was acidified to pH 2-3 with 1 N aqueous HCl. The resulting precipitate was collected, washed with water, and dried in vacuo to provide 17.7 g of 6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazine-3-thiol as a yellow solid (80.5% yield): 1H NMR (DMSO-d6) δ 3.95 (s, 3H), 7.73 (d, 1H), 8.13 (s, 1H), 8.16 (d, 1H), 8.53 (s, 1H), 14.7 (s, 1H); MS (m/z) 233 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h under nitrogen atmosphere
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in 1 N aqueous sodium hydroxide
  5. filtrationthe insolubles were filtered off
  6. customThe resulting precipitate was collected
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-186891776ddc4148b1e4ae08817c78f5
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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