Hydrazine hydrate (1:1) → 4-amino-N-methylbenzene-1-sulfonamide

HRID 57231

Reaction equation

HRID 57231 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N-:13][CH3:14])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.O.NN>C(O)C.[Ni]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH3:14])(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866087554-Nitrobenzenesulfonyl methylamide

Product 1

HCID 743684-amino-N-methylbenzene-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of the crude 4-nitrobenzenesulfonyl methylamide prepared above in 45 mL of ethanol, was added a 1 mL slurry of Raney Nickel. Hydrazine monohydrate (18 mmol) was added slowly in several portions. A change in the solution colour from yellow to colourless indicated the reaction was complete. The mixture was stirred for an additional 1 hr. The solids were removed by filtration and the solvent was evaporated. The resulting crude material was purified by flash column chromatography eluting with CH2Cl2:MeOH=10:1 to yield 2.09 g (90% for two steps) of the title compound as a pale orange powder.

Workup

  1. customThe solids were removed by filtration
  2. customthe solvent was evaporated
  3. customThe resulting crude material was purified by flash column chromatography
  4. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-2af18a93124e4b66859e501bec395da1
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Linked notes

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