1-Bromo-2-butanone → HCID 69209254, compound

HRID 30653

Reaction equation

HRID 30653 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](=[S:14])[NH2:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:16][C:17](=O)[CH2:18][CH3:19]>C(O)(C)(C)C>[CH2:18]([C:17]1[N:13]=[C:12]([CH2:11][CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[S:14][CH:16]=1)[CH3:19]

Participants

4

Reactant 2

HCID 131561-Bromo-2-butanoneHCID 826731463-(4-Nitrophenyl)propanethioamide

Product 1

HCID 69209254HCID 69209254, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 3-(4-nitrophenyl)propanethioamide (1.25 g), 1-bromo-2-butanone (0.98 g) and tert-butanol (30 mL) was heated under reflux for 30 min. The reaction mixture was concentrated, and saturated aqueous sodium hydrogen carbonate was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 4-ethyl-2-[2-(4-nitrophenyl)ethyl]-1,3-thiazole as a yellow oil (1.48 g, yield 95%) from a fraction eluted with hexane-ethyl acetate (4:1-2:1, v/v).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 min
  3. concentrationThe reaction mixture was concentrated
  4. additionsaturated aqueous sodium hydrogen carbonate was added to the residue
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bce00eac5075431fb0aeab203b251a1e
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

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