Sodium Hydroxide → (3-Methanesulfonylphenyl)hydrazine

HRID 985557Notes

Reaction equation

HRID 985557 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([NH2:11])[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[N:12]([O-])=O.[Na+].Cl.NN.[OH-].[Na+]>Cl.O>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([NH:11][NH2:12])[CH:8]=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 115031Hydrazinium chlorideHCID 4280293-(Methylsulphonyl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 22034382(3-Methanesulfonylphenyl)hydrazine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent3×HCID 962WaterSolvent

Procedure

To a solution of 3-methanesulphonyl-phenylamine (2.5 g) in 6 mL HCl was added a solution of NaNO2 in 5 mL of H2O at −5° to 0° C. After stirring for 30 min the resulted diazonium salt was poured into a cold solution (−10° to −15° C.) of stannous chloride in 6 ml HCl. The mixture of resulted hydrazine hydrochloride in HCl was stored in the refrigerator overnight. The solution was basified to pH 10, by addition of a 6N solution of NaOH, and extracted with THF. The organic layer was washed, dried over MgSO4, and evaporated to yield 2 g of a light brown solid (3-methanesulfonyl-phenyl)-hydrazine.

Workup

  1. customwas stored in the refrigerator overnight
  2. extractionextracted with THF
  3. washThe organic layer was washed
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-1f9327ce142e42c6b9c939675f57aa34
Source dataset
uspto-grants-2005_03
Patent number
US06872744B2

Reaction notes

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