Acetic Acid → HCID 11312013, compound

HRID 1633802Notes

Reaction equation

HRID 1633802 reaction equation
C(O)(=[O:3])C.S(=O)(=O)(O)O.O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:29])[C:19]([NH:21][C:22]([C:27]#N)([CH3:26])[CH:23]([CH3:25])[CH3:24])=[O:20])=[CH:14][CH:13]=1>C(OCC)(=O)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([C:19]2[O:20][C:26](=[O:3])[C:22]([CH:23]([CH3:25])[CH3:24])([CH3:27])[N:21]=2)[CH3:29])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962Water2×HCID 1118Sulfuric AcidHCID 186801792-(4-chlorophenyl)-N-(1-cyano-1,2-dimethylpropyl)propanamide

Product 1

HCID 11312013HCID 11312013, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

40 ml of glacial acetic acid, 1.96 g (0.019 mole) of concentrated sulfuric acid and 0.36 g (0.02 mole) of water were added to 5.56 g (0.02 mole) of 2-(4-chlorophenyl)-N-(1-cyano-1,2-dimethylpropyl)propanamide. The mixture was stirred at 60° C. for 2 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was cooled. Thereto were added 400 ml of water and 400 ml of ethyl acetate for layer separation. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and concentrated to obtain 5.58 g of 2-[1-(4-chlorophenyl)ethyl]-4-isopropyl-4-methyl-1,3-oxazol-5-one (yield=100%).

Workup

  1. customto give rise
  2. customto a reaction
  3. customAfter the completion of the reaction
  4. temperaturethe reaction mixture was cooled
  5. customfor layer separation
  6. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
  7. concentrationa saturated aqueous sodium chloride solution, and concentrated

Sources & evidence

ORD record
ord-ec339a86d8a94b1886f1c1ed8e8d1474
Source dataset
uspto-grants-2003_01
Patent number
US06504046B1

Reaction notes

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