Carbon Disulfide → HCID 178480034, compound

HRID 2386588Notes

Reaction equation

HRID 2386588 reaction equation
[NH:1]([C:3]1[N:4]=[N:5][C:6]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[CH:7][CH:8]=1)[NH2:2].[OH-].[K+].[C:17](=S)=[S:18]>C(O)C.O>[CH3:14][N:12]1[CH:13]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]3[N:4]([C:17]([SH:18])=[N:2][N:1]=3)[N:5]=2)[CH:10]=[N:11]1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 580751723-Hydrazinyl-6-(1-methyl-1H-pyrazol-4-yl)pyridazine

Product 1

HCID 178480034HCID 178480034, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
63.5 °C

Procedure

To a solution of 3-hydrazinyl-6-(1-methyl-1H-pyrazol-4-yl)pyridazine (53 g, 278.6 mmol) in ethanol (550 ml) is added an aqueous solution of KOH (17.2 g, 306.6 mmol) in water (130 mL), followed by CS2 (36 mL, 596.7 mmol). The mixture is stirred at 60-67° C. for 3 h under N2 atmosphere and cooled to RT. Solvents are removed under vacuum and the residue is dissolved in 1N aqueous NaOH (350 mL). The insolubles are filtered off and the filtrate is acidified to pH 2-3 with 1N aqueous HCl. The precipitate is collected, washed with water, and dried under vacuum to provide the title compound (50 g, 77.3%). MS (m/z): 233.0 (M+H).

Workup

  1. temperaturecooled to RT
  2. customSolvents are removed under vacuum
  3. dissolutionthe residue is dissolved in 1N aqueous NaOH (350 mL)
  4. filtrationThe insolubles are filtered off
  5. customThe precipitate is collected
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-d71e9ac7fb8d43c09d0fc93519d51ec1
Source dataset
uspto-grants-2012_09
Patent number
US08268836B2

Reaction notes

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