Acetic Anhydride → (2-Acetamido-1,3-thiazol-4-yl)methyl acetate

HRID 2109695Notes

Reaction equation

HRID 2109695 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][OH:8])[N:6]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10].[O:16]1CCO[CH2:18][CH2:17]1>>[C:9]([O:8][CH2:7][C:5]1[N:6]=[C:2]([NH:1][C:17](=[O:16])[CH3:18])[S:3][CH:4]=1)(=[O:11])[CH3:10]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 312751,4-DioxaneHCID 16766621(2-Amino-1,3-thiazol-4-yl)methanol

Product 1

HCID 14931747(2-Acetamido-1,3-thiazol-4-yl)methyl acetateYield 30%

Procedure

2-Aminothiazol-4-yl-methanol (17 g, 131 mmol) and acetic anhydride (927 g, 261 mmol) were mixed in 100 mL dioxane in a 500 mL round bottom flask. The mixture was heated at reflux for 1 hour. After the solvent was evaporated, 300 mL saturated sodium bicarbonate was added to the flask. The mixture was extracted twice with 200 mL EtOAc. The combined organic layers were washed with brine and dried over sodium sulfate. After evaporating the solvent, the remaining residue was washed with hexane and ether three times each. This procedure provided 10 g of (2-acetamidothiazol-4-yl)methyl acetate (yield=30%). LCMS (API-ES) m/z (%) 215.2 (100%, M++H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customAfter the solvent was evaporated
  4. addition300 mL saturated sodium bicarbonate was added to the flask
  5. extractionThe mixture was extracted twice with 200 mL EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. customAfter evaporating the solvent
  9. washthe remaining residue was washed with hexane and ether three times each

Sources & evidence

ORD record
ord-114ff77c61ca449c9436925a0440f25e
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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