Ethanol → Ethyl 3-[4-(2-benzofuranyl)thiazol-2-yl]propionate

HRID 2269707Notes

Reaction equation

HRID 2269707 reaction equation
Br[CH2:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)=O.[CH2:14](O)C.[NH2:17][C:18](=[S:25])[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22]>O>[O:6]1[C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=[C:5]1[C:3]1[N:17]=[C:18]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:14])=[O:22])[S:25][CH:2]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 27354511-(1-Benzofuran-2-Yl)-2-Bromoethan-1-OneHCID 18333020Methyl 4-amino-4-thioxobutanoate

Product 1

HCID 18333015Ethyl 3-[4-(2-benzofuranyl)thiazol-2-yl]propionate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(Bromoacetyl)benzofuran (650 ml) was added to an ethanol (12 ml) solution of methyl 4-amino-4-thioxobutyrate (400 mg), which was heated under reflux overnight. After cooling, water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was dried, concentrated, and then purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1). The obtained crystals were washed with hexane to obtain ethyl 3-[4-(2-benzofuranyl)thiazol-2-yl]propionate (460 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. extractionwas extracted with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1)
  8. washThe obtained crystals were washed with hexane

Sources & evidence

ORD record
ord-81ba8f4e2d634cbfbf9dcde51199b65d
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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