Dimethylformamide → 2-Hydroxy-4-phenylthiazole

HRID 1397364Notes

Reaction equation

HRID 1397364 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[S-:11][C:12]#[N:13].[K+].CN(C=[O:19])C>[I-].[K+]>[C:5]1([C:3]2[NH:13][C:12](=[O:19])[S:11][CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6259Phenacyl bromideHCID 516872Potassium thiocyanate

Product 1

HCID 6989032-Hydroxy-4-phenylthiazoleYield 75%

Reagents, catalysts & solvents 1

HCID 4875Potassium IodideCatalyst

Conditions

Temperature
80 °C

Procedure

A suspension of 2-bromoacetophenone (5 g, 0.0251 mol), potassium thiocyanate (8.6 g, 0.088 mol) and potassium iodide (0.25 g, 0.0015 mol) in dry DMF (25 mL) was heated to 80° C. for 2 h. The reaction mixture was concentrated to dryness under reduced pressure and the residue was dissolved in glacial acetic acid (25 mL) and 50% aqueous H2SO4 was added to it. The reaction mixture was heated to 100° C. for 10 min. The reaction mixture was poured in ice water and the precipitate formed was filtered and dried under reduced pressure to get 4-phenylthiazol-2(3H)-one (3.3 g, yield 75%) as a brown solid, which was carried through without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. dissolutionthe residue was dissolved in glacial acetic acid (25 mL)
  3. addition50% aqueous H2SO4 was added to it
  4. temperatureThe reaction mixture was heated to 100° C. for 10 min
  5. additionThe reaction mixture was poured in ice water
  6. customthe precipitate formed
  7. filtrationwas filtered
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-747cd62c668945d9a9ceb632e061300e
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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