N-{4-[(Z)-2-(4-nitrophenyl)ethenyl]thiazol-2-yl}acetamide → N-{4-[2-(4-aminophenyl)ethyl]thiazol-2-yl}acetamide

HRID 2117833Notes

Reaction equation

HRID 2117833 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]\[C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.O1CCCC1.C(O)(=O)C.[C].[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 2

HCID 58720254N-{4-[(Z)-2-(4-nitrophenyl)ethenyl]thiazol-2-yl}acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 21914814N-{4-[2-(4-aminophenyl)ethyl]thiazol-2-yl}acetamideYield 29.9%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-{4-[(Z)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}acetamide (2 g) and 10% palladium carbon (400 mg) in methanol (25 ml), tetrahydrofuran (25 ml) and acetic acid (18 ml) was stirred under 4 atm hydrogen at ambient temperature for 5 hours. The reaction mixture was filtered through a celite pad, and the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate. The organic solution was washed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel with n-hexane/ethyl acetate (1:2)→ethyl acetate as an eluent, and triturated with ethyl alcohol/ethyl ether to give N-(4-(2-(4-aminophenyl)ethyl)-1,3-thiazol-2-yl)acetamide (539.6 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. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe organic solution was washed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography over silica gel with n-hexane/ethyl acetate (1:2)
  8. customtriturated with ethyl alcohol/ethyl ether

Sources & evidence

ORD record
ord-4f7a9523c8544872b6f155c3e8540b35
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

Loading…