N,N-diethyl-4-(5-nitrothiazol-2-yl)aniline → 2-(4-(Diethylamino)phenyl)thiazol-5-amine

HRID 56112Notes

Reaction equation

HRID 56112 reaction equation
[CH2:1]([N:3]([CH2:18][CH3:19])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]([N+:15]([O-])=O)=[CH:13][N:14]=2)=[CH:6][CH:5]=1)[CH3:2]>CO.[Pd]>[CH2:18]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]([NH2:15])=[CH:13][N:14]=2)=[CH:6][CH:5]=1)[CH3:19]

Participants

4

Reactant 1

HCID 90022668N,N-diethyl-4-(5-nitrothiazol-2-yl)aniline

Product 1

HCID 900236882-(4-(Diethylamino)phenyl)thiazol-5-amineYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N,N-diethyl-4-(5-nitrothiazol-2-yl)aniline (0.73 g, 2.64 mmol) in MeOH (30 mL) was added Pd/C (73 mg). The reaction mixture was stirred at rt under H2 overnight, then filtered. The filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=5:1) to give the title compound as a white solid (0.45 g, 69%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=5:1)

Sources & evidence

ORD record
ord-e5a212ed3518472fa2f3bcb1aed903dc
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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