N-[4-Methyl-5-(4-nitro-phenyl)-thiazol-2-yl]-acetamide → N-[5-(4-amino-phenyl)-4-methyl-thiazol-2-yl]-acetamide

HRID 601609Notes

Reaction equation

HRID 601609 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:16][C:17](=[O:19])[CH3:18])[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1>C(OCC)(=O)C.C1COCC1.[Pd]>[NH2:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]2[S:5][C:4]([NH:16][C:17](=[O:19])[CH3:18])=[N:3][C:2]=2[CH3:1])=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 11414740N-[4-Methyl-5-(4-nitro-phenyl)-thiazol-2-yl]-acetamide

Product 1

HCID 85861718N-[5-(4-amino-phenyl)-4-methyl-thiazol-2-yl]-acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

N-[4-Methyl-5-(4nitro-phenyl)-thiazol-2-yl]-acetamide (J. Liebscher, E. Mitzner, Synthesis, 1985, (4), p 414) (10.0 g, 3.6 mmol) is dissolved in ethyl acetate/THF (5/1, 600 ml) and stirred at room temperature under an atmosphere of argon. The solution is then treated with 10% palladium on carbon (10 g). The reaction mixture is purged three times with nitrogen and placed under an atmosphere of hydrogen overnight. The mixture is then filtered through Celite™ filter material and the catalyst is washed with tetrahydrofuran (600 ml). The solvent is removed in vacuo to leave N-[5-(4-amino-phenyl)4-methyl-thiazol-2-yl]-acetamide as an off-white solid.

Workup

  1. customThe reaction mixture is purged three times with nitrogen
  2. filtrationThe mixture is then filtered through Celite™
  3. filtrationfilter material
  4. washthe catalyst is washed with tetrahydrofuran (600 ml)
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-b6baaa8182cc494d80830c15479af59e
Source dataset
uspto-grants-2011_03
Patent number
US07902375B2

Reaction notes

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