Dimethylformamide → HCID 16791991, compound

HRID 2102807Notes

Reaction equation

HRID 2102807 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[S:10][C:6]=2[CH:5]=1)([O-])=O.CN(C)C=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:21]=[CH:20][C:7]2[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]3[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=3)[S:10][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 731722HCID 731722, compound

Product 1

HCID 16791991HCID 16791991, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-(6-Nitrobenzothiazol-2-yl)isonicotinamide (2.42 g, 8.04 mmol) was suspended in ethyl acetate (150 mL), and dimethylformamide was added until dissolution occured. After addition of palladium on charcoal (4.25 g, 10% Pd, 4 mmol Pd) the mixtue was hydrogenated (1 bar) at 60° C. until completion of the reaction. The palladium was removed by filtration through a pad of celite and the solvent was evaporated. The residue was taken up in little methanol and precipitated by addition of water to obtain N-(6-aminobenzothiazol-2-yl)isonicotinamide (1.73 g, 6.4 mmol, 80%). LC/ESI-MS: m/z=271 [M+H]+; m/z=269 [M−H]−; Rt=1.43 min.

Workup

  1. customat 60° C.
  2. customuntil completion of the reaction
  3. customThe palladium was removed by filtration through a pad of celite
  4. customthe solvent was evaporated
  5. customprecipitated by addition of water

Sources & evidence

ORD record
ord-cc9df3bb9de140138e37621292b69f26
Source dataset
uspto-grants-2009_08
Patent number
US07576090B2

Reaction notes

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