Bromine → HCID 57634191, compound

HRID 661125Notes

Reaction equation

HRID 661125 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, 2.9 mmol) 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-c33d978c64de40bda796cb2bbc09e41d
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

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