Phenacyl bromide → 2,4-Dimethyl-3-(2-oxo-2-phenylethyl)-1,3-thiazol-3-ium bromide

HRID 1836729Notes

Reaction equation

HRID 1836729 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.[Br:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11]>C(#N)C>[Br-:8].[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N+:6]=1[CH2:9][C:10](=[O:11])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 109342,4-Dimethylthiazole

Product 1

HCID 132127282,4-Dimethyl-3-(2-oxo-2-phenylethyl)-1,3-thiazol-3-ium bromideYield 70.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,4-Dimethylthiazole (0.5 g, 4.41 mmole), 2-bromo-1-phenyl-1-ethanone (0.879 g, 4.41 mmole), and acetonitrile (0.25 mL) were heated in an oil bath at 105 C. for 1.5 hr. Product precipitation began within 10 min. After cooling, acetonitrile (5 mL) and ether (4 mL) were added and the mixture stood at room temp. overnight. Filtration and washing with 30% ether/acetonitrile gave 1.2 g crude product which was recrystalized from methanol/acetonitrile/ether to afford 0.97 g of the title compound, mp 235-237 C (dec.).

Workup

  1. customProduct precipitation
  2. waitbegan within 10 min
  3. temperatureAfter cooling
  4. additionacetonitrile (5 mL) and ether (4 mL) were added
  5. waitthe mixture stood at room temp. overnight
  6. filtrationFiltration
  7. washwashing with 30% ether/acetonitrile
  8. customgave 1.2 g crude product which
  9. customwas recrystalized from methanol/acetonitrile/ether

Sources & evidence

ORD record
ord-ffbeaad1152543c39e4b3481a406372a
Source dataset
uspto-grants-2004_08
Patent number
US06777557B2

Reaction notes

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