Ethanol → 5-Isopropyl-4-(4-Methoxy-Phenyl)-2-Methyl-1,3-Thiazole

HRID 732243Notes

Reaction equation

HRID 732243 reaction equation
Br[CH:2]([CH:13]([CH3:15])[CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=O.C(O)C.[C:19]([NH2:22])(=[S:21])[CH3:20]>C(OC(=O)C)C>[CH:13]([C:2]1[S:21][C:19]([CH3:20])=[N:22][C:3]=1[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723949ThioacetamideHCID 578383622-bromo-1-(4-Methoxy-Phenyl)-3-Methyl-Butan-1-One

Product 1

HCID 578383635-Isopropyl-4-(4-Methoxy-Phenyl)-2-Methyl-1,3-ThiazoleYield 51%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

While 77.0 g of 2-bromo-1-(4-methoxy-phenyl)-3-methyl-butan-1-one (4) prepared in Example 2 were added to 200 ml of ethanol and stirred, 42.7 g of thioacetamide were added. Subsequently, the temperature was gradually increased and stirring under reflux was continued for 22 hr. After the reaction was completed, the resultant reaction mixture was added with 300 ml of ethylacetate, and then washed with a saturated aqueous solution of potassium carbonate. The ethylacetate layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure, thus obtaining 35.8 g (yield: 51.0%) of a title compound as brown liquid.

Workup

  1. temperatureSubsequently, the temperature was gradually increased
  2. stirringstirring
  3. temperatureunder reflux
  4. customthe resultant reaction mixture
  5. washwashed with a saturated aqueous solution of potassium carbonate
  6. dry with materialThe ethylacetate layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fbebe0d9b5754199a451b292c063aa26
Source dataset
uspto-grants-2009_09
Patent number
US07585979B2

Reaction notes

Loading…