4-Hydroxybenzaldehyde → N-{4-[2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-2-yl}acetamide

HRID 1892468Notes

Reaction equation

HRID 1892468 reaction equation
[Br-].[C:2]([NH:5][C:6]1[S:7][CH:8]=[C:9]([CH2:11][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:10]=1)(=[O:4])[CH3:3].[OH:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1.CC(C)([O-])C.[K+].O>CN(C)C=O.C(OCC)(=O)C>[OH:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=[CH:11][C:9]2[N:10]=[C:6]([NH:5][C:2](=[O:4])[CH3:3])[S:7][CH:8]=2)=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86649976{[2-(Acetylamino)-1,3-thiazol-4-yl]methyl}(triphenyl)phosphoniumbromide

Product 1

HCID 86649975N-{4-[2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-2-yl}acetamideYield 67.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

{[2-(Acetylamino)-1,3-thiazol-4-yl]methyl}(triphenyl)phosphoniumbromide (261.1 mg, 0.525 mmol) and 4-hydroxybenzaldehyde (183.2 mg, 1.50 mmol) were dissolved in anhydrous N,N-dimethylformamide (2 ml), and potassium tert-butoxide (56.1 mg, 0.50 mmol) was added at 0° C. After stirring at 90° C. for 12 hr, the mixture was cooled to room temperature. Water and ethyl acetate were added, and the mixture was stirred, stood still and then partitioned. The aqueous layer was extracted with ethyl acetate, and the combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 25 g, ethyl acetate:hexane=4:6→5:5) to give N-{4-[2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-2-yl}acetamide (87.9 mg, 0.338 mmol, yield 67.5%) as a white solid.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. stirringthe mixture was stirred
  3. custompartitioned
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrated residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 25 g, ethyl acetate:hexane=4:6→5:5)

Sources & evidence

ORD record
ord-53ad155279014c1e90fc49674a105a18
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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