Dimethylformamide → N-(6-amino-1,3-benzothiazol-2-yl)benzamide

HRID 2102806Notes

Reaction equation

HRID 2102806 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][CH:16]=[CH:15][CH:14]=3)[S:10][C:6]=2[CH:5]=1)([O-])=O.CN(C)C=O>[Pd].C(OCC)(=O)C>[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:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[S:10][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 1548453N-(6-nitro-1,3-benzothiazol-2-yl)benzamide

Product 1

HCID 810331N-(6-amino-1,3-benzothiazol-2-yl)benzamideYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(6-nitrobenzothiazol-2-yl)benzamide (3.77 g, 12.6 mmol), palladium on charcoal (2 g, 10% Pd, 1.88 mmol Pd), dimethyl formamide (80 mL) and ethyl acetate (20 mL) was hydrogenated (1 bar) for 2 h at 60° C. The palladium was removed by filtration through a pad of celite. After concentration to 20 mL, water was added and the resulting precipitate was separated by filtration to obtain N-(6-aminobenzothiazol-2-yl)-benzamide (3.15 g, 11.7 mmol, 93%) as a grey solid. LC/ESI-MS: m/z=270 [M+H]+; m/z=268 [M−H]−; Rt=2.27 min.

Workup

  1. customfor 2 h
  2. customat 60° C
  3. customThe palladium was removed by filtration through a pad of celite
  4. concentrationAfter concentration to 20 mL, water
  5. additionwas added
  6. customthe resulting precipitate was separated by filtration

Sources & evidence

ORD record
ord-ed3a273bca7244e7abdb049d112b86a6
Source dataset
uspto-grants-2009_08
Patent number
US07576090B2

Reaction notes

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