Carbon Disulfide → HCID 178527924, compound

HRID 1890962Notes

Reaction equation

HRID 1890962 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[OH-].[K+].[C:12](=S)=[S:13]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:12]([SH:13])=[N:9][N:8]=2)[N:7]=1

Participants

6

Reactant 3

HCID 6348Carbon Disulfide2×HCID 14797Potassium Hydroxide2×HCID 1007873-Chloro-6-hydrazinopyridazine

Product 1

HCID 178527924HCID 178527924, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of (6-chloro-pyridazin-3-yl)-hydrazine (1 g, 6.917 mmol) in ethanol (12 mL) was added a solution of KOH (390 mg, 6.917 mmol) in water (12 mL) dropwise. Carbon disulfide (0.84 mL, 13.84 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 48 h. Another 0.84 mL CS2 and 390 mg KOH were added, and the reaction mixture was further stirred for 24 h, before concentrating in vacuo. The residue was treated with 1 M aqueous NaOH and filtered. The filtrate was acidified to pH 3 with 1 N aqueous HCl, and the precipitate was filtered off. The resulting filtrate was extracted with ethyl acetate (3×), and the combined organics were dried over sodium sulfate, filtered, concentrated and dried in vacuo to provide 485 mg of 6-chloro-[1,2,4]triazolo[4,3-b]pyridazine-3-thiol as a yellow solid (38% yield): 1H NMR (DMSO-d6): δ 7.48 (d, 1H), 8.24 (d, 1H); MS (m/z) 187 [M+H+]+.

Workup

  1. stirringthe reaction mixture was further stirred for 24 h
  2. concentrationbefore concentrating in vacuo
  3. additionThe residue was treated with 1 M aqueous NaOH
  4. filtrationfiltered
  5. filtrationthe precipitate was filtered off
  6. extractionThe resulting filtrate was extracted with ethyl acetate (3×)
  7. dry with materialthe combined organics were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customdried in vacuo

Sources & evidence

ORD record
ord-9255925341c64c3f97db1ee51c42cd70
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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