Phenacyl bromide → 4-(4-Phenyl-1,3-thiazol-2-yl)phenol

HRID 49375Notes

Reaction equation

HRID 49375 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[OH:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[S:17])=[CH:14][CH:13]=1>C(O)C>[C:5]1([C:3]2[N:18]=[C:16]([C:15]3[CH:19]=[CH:20][C:12]([OH:11])=[CH:13][CH:14]=3)[S:17][CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 27593444-Hydroxythiobenzamide

Product 1

HCID 1356483144-(4-Phenyl-1,3-thiazol-2-yl)phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
35 °C

Procedure

In a round-bottomed flask, 2-bromoacetophenone (520 mg, 2.61 mmol) and 4-hydroxy-thiobenzamide (400 mg, 2.61 mmol) were dissolved in ethanol (10 ml), and the resulting solution was heated to reflux. After about one hour, the reaction was cooled to about 35° C. and was allowed to stir for about an additional twelve hours. The reaction mixture was then concentrated in vacuo to an oil, the residue redissolved in ethyl acetate and methylene chloride, and extracted with saturated aqueous sodium bicarbonate. The combined extracts were then extracted with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to an oil. The crude product was purified by column chromatography (silica gel; methylene chloride to 2% methanol/methylene chloride). The title product was isolated as a white solid (516 mg, 78% yield). LRMS ([M+H]+)=254.1.

Workup

  1. temperaturethe resulting solution was heated to reflux
  2. concentrationThe reaction mixture was then concentrated in vacuo to an oil
  3. dissolutionthe residue redissolved in ethyl acetate
  4. extractionmethylene chloride, and extracted with saturated aqueous sodium bicarbonate
  5. extractionThe combined extracts were then extracted with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to an oil
  9. customThe crude product was purified by column chromatography (silica gel; methylene chloride to 2% methanol/methylene chloride)

Sources & evidence

ORD record
ord-efc415e43d7e4042b2102927f433ae86
Source dataset
uspto-grants-2004_03
Patent number
US06706743B2

Reaction notes

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