HCID 86595596, compound → HCID 21915113, compound

HRID 2117877Notes

Reaction equation

HRID 2117877 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]\[C:12]2[S:16][C:15]([NH:17][C:18](=[O:20])[CH3:19])=[N:14][CH:13]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(OCC)(=O)C.CN(C)C=O.[C].[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[S:16][C:15]([NH:17][C:18](=[O:20])[CH3:19])=[N:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 86595596HCID 86595596, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21915113HCID 21915113, compoundYield 26.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-{5-[(Z)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}acetamide (1 g) and 10% palladium carbon (1.04 g) in ethyl acetate (100 ml) and N,N-dimethylformamide (20 ml) was stirred under 4 atm hydrogen at ambient temperature for 4hours. The reaction mixture was filtered through a celite pad, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with chloroform/methanol (30:1→20:1) as an eluent, and triturated with ethyl ether to give N-{5-[2-(4-aminophenyl)ethyl]-1,3-thiazol-2-yl}acetamide (240.9 mg) as an off-white solid.

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash column chromatography over silica gel with chloroform/methanol (30:1→20:1) as an eluent
  4. customtriturated with ethyl ether

Sources & evidence

ORD record
ord-bf6f0169bdfb479e992b52d6ce5daf7a
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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