Acibenzolar Acid Impurity 21 → 7-Aminomethylbenzo-1,2,3-thiadiazole

HRID 257141Notes

Reaction equation

HRID 257141 reaction equation
[C:1]([C:3]1[C:11]2[S:10][N:9]=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)#[N:2].[H][H]>CO.[Ni]>[NH2:2][CH2:1][C:3]1[C:11]2[S:10][N:9]=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 22182879Acibenzolar Acid Impurity 21HCID 178418361HCID 178418361, compound3×

Product 1

HCID 197845907-Aminomethylbenzo-1,2,3-thiadiazole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In a hydrogenation vessel, a solution of 14.5 g of 7-cyanobenzo-1,2,3-thiadiazole in 150 ml of methanol is treated with 4.4 g of Raney nickel and with 15 g of liquid nitrogen. Hydrogen is subsequently injected, the vessel is heated, and the mixture is hydrogenated at 60° C. and constant hydrogen pressure of 107Pa until hydrogen is no longer taken up. The mixture is then cooled, the catalyst is removed by filtration, the filtrate is evaporated and chromatographed on silica gel (hexane/ethyl acetate 2:1), resulting in the title compound of m.p. 136°-139° C.).

Workup

  1. temperaturethe vessel is heated
  2. customis hydrogenated at 60° C.
  3. temperatureThe mixture is then cooled
  4. customthe catalyst is removed by filtration
  5. customthe filtrate is evaporated
  6. customchromatographed on silica gel (hexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-abd16ce201a9460da9e3b077dba8a988
Source dataset
uspto-grants-1993_11
Patent number
US05260423

Reaction notes

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