1,3-Dichloroacetone → 4-(Chloromethyl)-2-phenyl-1,3-thiazole

HRID 1044065Notes

Reaction equation

HRID 1044065 reaction equation
[C:1](=[S:9])([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][CH2:11][C:12](=O)[CH2:13]Cl>CCO.C1COCC1>[Cl:10][CH2:11][C:12]1[N:8]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:9][CH:13]=1

Participants

5

Reactant 2

HCID 107931,3-DichloroacetoneHCID 683563Thiobenzamide

Product 1

HCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazoleYield 72.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Benzothioamide (0.8 g, 5.83 mmol) was dissolved in a mixture EtOH (26.0 ml) and THF (10.4 ml), and the solution was heated to 65° C. 1,3-Dichloropropan-2-one (0.81 g, 6.41 mmol) was added, and the mixture was heated to reflux overnight (UPLC-MS: complete conversion). The solvents were evaporated, and the residue was taken up with EtOAc (100 ml) and washed with an aqueous solution of NaHCO3. The organic phase was dried (Na2SO4), filtered and evaporated to dryness. The crude was purified by flash chromatography eluting with petroleum ether/EtOAc=97/3 to obtain 4-chloromethyl-2-phenyl-thiazole (891 mg, 72.9% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight (UPLC-MS: complete conversion)
  3. customThe solvents were evaporated
  4. washwashed with an aqueous solution of NaHCO3
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude was purified by flash chromatography
  9. washeluting with petroleum ether/EtOAc=97/3

Sources & evidence

ORD record
ord-11f6e098b96b452ca4a38995e224af23
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

Loading…