1-Chloro-3-fluoro-propan-2-one → N-(4-(fluoromethyl)thiazol-2-yl)acetamide

HRID 444884

Reaction equation

HRID 444884 reaction equation
Cl[CH2:2][C:3](=O)[CH2:4][F:5].[C:7]([NH:10][C:11]([NH2:13])=[S:12])(=[O:9])[CH3:8]>CCO>[F:5][CH2:4][C:3]1[N:13]=[C:11]([NH:10][C:7](=[O:9])[CH3:8])[S:12][CH:2]=1

Participants

4

Reactant 2

HCID 2283961-Chloro-3-fluoro-propan-2-oneHCID 2723593Acetylthiourea

Product 1

HCID 59293708N-(4-(fluoromethyl)thiazol-2-yl)acetamideYield 8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-chloro-3-fluoro-propan-2-one (Step 38.3) (1.14 g, 10.3 mmol) and N-acetyl-2-thiourea (1.22 g, 10.3 mmol) in EtOH (10 mL) is stirred for 1.5 h at reflux, allowed to cool and concentrated. The residue is dissolved in DCM/H2O and extracted with DCM. The organic phase is dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (Hex/EtOAc, 1:1) to afford 0.143 g of the title compound: ESI-MS: 173.1 [M−H]−; tR=1.98 min (System 1); TLC: Rf=0.21 (Hex/EtOAc, 1:1).

Workup

  1. temperatureat reflux
  2. temperatureto cool
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in DCM/H2O
  5. extractionextracted with DCM
  6. dry with materialThe organic phase is dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified by silica gel column chromatography (Hex/EtOAc, 1:1)

Sources & evidence

ORD record
ord-ea5528d5730043618f9ddc984d6bad1b
Source dataset
uspto-grants-2013_07
Patent number
US08476268B2

Linked notes

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