Hydrazine → N-(4-aminobenzyl)ethanesulfonamide

HRID 2236928Notes

Reaction equation

HRID 2236928 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][NH:9][S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.NN>[Ni].CO>[NH2:1][C:4]1[CH:16]=[CH:15][C:7]([CH2:8][NH:9][S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 47372696N-(4-nitrobenzyl)ethanesulfonamide

Product 1

HCID 39243426N-(4-aminobenzyl)ethanesulfonamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To the residue of the product from step 1 (0.25 mmol) is added methanol (350 μL), hydrazine (33 μL), and Raney-Nickel (10 mg). The reaction mixture is shaken at room temperature for 16 hours, then filtered and the solution concentrated to yield ethanesulfonic acid 4-amino-benzylamide, which is used as such for the subsequent reaction.

Workup

  1. filtrationfiltered
  2. concentrationthe solution concentrated

Sources & evidence

ORD record
ord-56f987b31f4c49e5bdcb88db96800530
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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