Bromine → HCID 57634191, compound

HRID 2109796Notes

Reaction equation

HRID 2109796 reaction equation
[Br:1]Br.[C:3]([O:6][CH2:7][CH2:8][C:9]1[N:10]=[C:11]([NH:14][C:15](=[O:17])[CH3:16])[S:12][CH:13]=1)(=[O:5])[CH3:4]>CC(O)=O>[C:3]([O:6][CH2:7][CH2:8][C:9]1[N:10]=[C:11]([NH:14][C:15](=[O:17])[CH3:16])[S:12][C:13]=1[Br:1])(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 24408BromineHCID 57634073HCID 57634073, compound

Product 1

HCID 57634191HCID 57634191, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Br2 (0.46 g, 2.9mmol) was dropped into 2-(2-acetamidothiazol-4-yl)ethyl acetate (0.60 g, 2.6 mmol) in 20 mL AcOH. The reaction was instantaneous. Acetic acid was evaporated from the reaction and saturated sodium bicarbonate was slowly added to the residue. The resulting mixture was extracted twice with EtOAc. The organic layer was washed with brine and dried over sodium sulfate. 2-(2-Acetamido-5-bromothiazol-4-yl)ethyl acetate (0.6 g, yield=74.3%) was obtained as a white solid. LCMS (API-ES) m/z (%): 309.0 (100%, M++H).

Workup

  1. customAcetic acid was evaporated from the reaction and saturated sodium bicarbonate
  2. additionwas slowly added to the residue
  3. extractionThe resulting mixture was extracted twice with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-16312b62bd5741278b070683af1525a1
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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