Hydrochloric Acid → 1-(5-Bromo-1,3-thiazol-2-yl)ethan-1-one

HRID 877365Notes

Reaction equation

HRID 877365 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7](OC)([O:9]C)[CH3:8])=[N:4][CH:3]=1.Cl>CC(C)=O.O>[Br:1][C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58974831HCID 58974831, compound

Product 1

HCID 299397331-(5-Bromo-1,3-thiazol-2-yl)ethan-1-oneYield 87.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 5-bromo-2-(1,1-dimethoxyethyl)-1,3-thiazole (35 g) was dissolved in acetone (200 ml) and water (200 ml), was added con. HCl (40 ml). The mixture was stirred for 5 h at room temperature. After concentration to remove acetone, the residue was adjusted to pH=7 by the addition of NaHCO3 and extracted with ether (30 ml×3). The organic layers were washed with brine, dried over Na2SO4 and concentrated to afford 25 g of 1-(5-bromo-1,3-thiazol-2-yl)ethanone as solid (87.4%). 1H-NMR (CDCl3 400 MHz) δ 7.87 (s, 1H, Ar—H), 2.66 (s, 3H, —CH3)

Workup

  1. concentrationAfter concentration
  2. customto remove acetone
  3. additionthe residue was adjusted to pH=7 by the addition of NaHCO3
  4. extractionextracted with ether (30 ml×3)
  5. washThe organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-266e4b1777a9464ebbb59708489f5437
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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