2-Bromo-1-(4-hydroxyphenyl)ethanone → HCID 19773531, compound

HRID 1614328Notes

Reaction equation

HRID 1614328 reaction equation
[C:1](=[S:5])([NH2:4])[CH2:2][CH3:3].Br[CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)=O>C(O)C>[CH2:2]([C:1]1[S:5][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[N:4]=1)[CH3:3]

Participants

4

Reactant 2

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneHCID 2760628Propanethioamide

Product 1

HCID 19773531HCID 19773531, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.6 parts of propanethioamide, 8.6 parts of 2-bromo-1-(4-hydroxyphenyl)ethanone and 79 parts of ethanol was stirred for 7 hours at reflux temperature. The reaction mixture was concentrated to 1/4 of its volume and 2,2'-oxybispropane was added to the residue. The precipitate was filtered off and taken up in water. After basifying with NH4OH, the product was extracted with dichloromethane. The extract was dried, filtered and evaporated, yielding 3.3 parts (40.2%) of 4-(2-ethyl-4-thiazolyl)-phenol (interm. 17).

Workup

  1. temperatureat reflux temperature
  2. concentrationThe reaction mixture was concentrated to 1/4 of its volume and 2,2'-oxybispropane
  3. additionwas added to the residue
  4. filtrationThe precipitate was filtered off
  5. extractionthe product was extracted with dichloromethane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-406989842834482181bf0fcd3d038624
Source dataset
uspto-grants-1993_03
Patent number
US05196535

Reaction notes

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