Sodium Hydroxide → 3-Hydrazino-1-methyl-5-methylmercaptopyrazole

HRID 362662Notes

Reaction equation

HRID 362662 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:10]=[C:9]([S:11][CH3:12])[N:8]([CH3:13])[N:7]=1.O.O.Cl[Sn]Cl.[OH-].[Na+]>O.Cl>[NH:5]([C:6]1[CH:10]=[C:9]([S:11][CH3:12])[N:8]([CH3:13])[N:7]=1)[NH2:1]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 23668193Sodium NitriteHCID 542284381-Methyl-5-(methylthio)-1H-pyrazol-3-amine

Product 1

HCID 451213143-Hydrazino-1-methyl-5-methylmercaptopyrazoleYield 96.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

1.1 g (15.8 mmol) sodium nitrite in 4 ml water was added dropwise to 1.9 g (13.1 mmol) 3-amino-1-methyl-5-methylmercaptopyrazole in 28 ml concentrated hydrochloric acid at 0° C. and the mixture stirred for 2 hours at 0° C. Then, at -30° C., a solution of 7.4 g (32.8 mmol) SnCl2.2H2O in 5.5 ml concentrated hydrochloric acid was added dropwise and the mixture stirred for 3 hours at this temperature. The reaction mixture was then made basic with 32% caustic soda and extracted with methylene chloride. The organic phase was dried over sodium sulfate and concentrated. 2.0 g of product was obtained which was used without further purification.

Workup

  1. stirringthe mixture stirred for 3 hours at this temperature
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6e4607a14e90497497466146eaf69488
Source dataset
uspto-grants-1999_02
Patent number
US05869686

Reaction notes

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