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

HRID 2117832Notes

Reaction equation

HRID 2117832 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[K+].[CH:37]([C:39]1[N:40]=[C:41]([NH:44][C:45](=[O:47])[CH3:46])[S:42][CH:43]=1)=O>CN(C)C=O>[N+:9]([C:6]1[CH:7]=[CH:8][C:3](/[CH:2]=[CH:37]\[C:39]2[N:40]=[C:41]([NH:44][C:45](=[O:47])[CH3:46])[S:42][CH:43]=2)=[CH:4][CH:5]=1)([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 660114-Nitrobenzyl bromideHCID 14931749N-(4-Formyl-1,3-thiazol-2-YL)acetamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 58720254N-{4-[(Z)-2-(4-nitrophenyl)ethenyl]thiazol-2-yl}acetamideYield 62.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(Bromomethyl)-4-nitrobenzene (1.9 g), triphenylphosphine (2.31 g) and N,N-dimethylformamide (20 ml) were combined under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 2.5 hours. Then potassium tert-butoxide (1.19 g) and N-(4-formyl-1,3-thiazol-2-yl)acetamide (1.5 g) were added and the mixture was stirred at room temperature for 14 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with 1N-hydrochloric acid, water 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 (1:1)-→(1:2) as an eluent, and triturated with ethyl ether to give N-{4-[(Z)-2-(4-nitrophenyl)ethenyl]-1,3-thiazol-2-yl}acetamide (1.59 g) as a yellow solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 14 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 1N-hydrochloric acid, water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography over silica gel with n-hexane/ethyl acetate (1:1)-→(1:2) as an eluent
  7. customtriturated with ethyl ether

Sources & evidence

ORD record
ord-4065306d42d34d8e9b6d49e028139f96
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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