Bromine → (2-Acetamido-5-bromothiazol-4-yl)methyl acetate

HRID 661023Notes

Reaction equation

HRID 661023 reaction equation
[C:1]([O:4][CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12](=[O:14])[CH3:13])[S:9][CH:10]=1)(=[O:3])[CH3:2].[Br:15]Br.C(OCC1N=C(NC(=O)C)SC=1)(=O)C.CC(O)=O>CC(O)=O>[C:1]([O:4][CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12](=[O:14])[CH3:13])[S:9][C:10]=1[Br:15])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 14931747(2-Acetamido-1,3-thiazol-4-yl)methyl acetateHCID 86613765(2-acetamidothiazol-4-yl)methyl acetate AcOH

Product 1

HCID 57633964(2-Acetamido-5-bromothiazol-4-yl)methyl acetateYield 81.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

(2-Acetamidothiazol-4-yl)methyl acetate (9.00 g, 42 mmol) was dissolved in 30 mL AcOH. A mixture of Br2 (9.0 g, 56.7 mmol) in 20 mL AcOH was added dropwise to the (2-acetamidothiazol-4-yl)methyl acetate/AcOH mixture. The reaction was complete in 10 minutes. After 200 mL distilled water was added to the reaction mixture, the mixture was extracted with EtOAc. The organic layer was washed a few times with water and saturated sodium bicarbonate. The organic layer was then washed with brine solution and dried over sodium sulfate. Evaporation of the solvent provided the product as a yellow solid (10 g, yield=80%). LCMS (API-ES) m/z (%) 293.2 (100%, M++H).

Workup

  1. distillationAfter 200 mL distilled water
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted with EtOAc
  4. washThe organic layer was washed a few times with water and saturated sodium bicarbonate
  5. washThe organic layer was then washed with brine solution
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-bbab8979f1244d7097d320debcb4d89a
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

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