Hydrochloric Acid → HCID 178423528, compound

HRID 1890956Notes

Reaction equation

HRID 1890956 reaction equation
[OH-].[K+].[CH3:3][C:4]1[N:9]=[N:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.[C:12](=S)=[S:13].Cl>CO>[CH3:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:12]([SH:13])=[N:11][N:10]=2)[N:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 123798043-Hydrazinyl-6-methylpyridazine

Product 1

HCID 178423528HCID 178423528, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of KOH (11.3 g, 0.202 mol) in methanol (100 mL) was added (6-methyl-pyridazin-3-yl)-hydrazine (25 g, 0.202 mol) at room temperature. The reaction mixture was placed in an ice-water bath and carbon disulfide (98 mL, 1.61 mol) was slowly added. The resultant yellow solution was heated to reflux overnight before removal of solvent. The yellow residue was acidified with 2 N aqueous HCl to pH˜4, filtered, and washed with water. Upon drying 33 g of 6-methyl-[1,2,4]triazolo[4,3-b]pyridazine-3-thiol was obtained as a yellow powder (85% yield): 1H NMR (DMSO-d6): δ 2.5 (s, 3H), 7.28 (d, 1H), 8.05 (d, 1H), 14.66 (br s, 1H); MS (m/z) 167 [M+H+]+.

Workup

  1. customThe reaction mixture was placed in an ice-water bath
  2. temperatureThe resultant yellow solution was heated
  3. temperatureto reflux overnight before removal of solvent
  4. filtrationfiltered
  5. washwashed with water
  6. dry with materialUpon drying 33 g of 6-methyl-[1,2,4]triazolo[4,3-b]pyridazine-3-thiol

Sources & evidence

ORD record
ord-81c474d0a5c14922991fc6ceec5dfcda
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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