Sulfuric Acid → HCID 11312013, compound

HRID 1633803Notes

Reaction equation

HRID 1633803 reaction equation
C1(C)C=CC=CC=1.S(=O)(=O)(O)O.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:31])[C:21]([NH:23][C:24]([C:29]#N)([CH3:28])[CH:25]([CH3:27])[CH3:26])=[O:22])=[CH:16][CH:15]=1.[OH-:32].[Na+]>O.C(O)(=O)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([C:21]2[O:22][C:28](=[O:32])[C:24]([CH:25]([CH3:27])[CH3:26])([CH3:29])[N:23]=2)[CH3:31])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 14798Sodium HydroxideHCID 186801792-(4-chlorophenyl)-N-(1-cyano-1,2-dimethylpropyl)propanamide

Product 1

HCID 11312013HCID 11312013, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

450 ml of toluene, 45 g (0.44 mole) of concentrated sulfuric acid and 45 ml of glacial acetic acid were added to 126.7 g (0.45 mole) of 2-(4-chlorophenyl)-N-(1-cyano-1,2-dimethylpropyl)propanamide. The mixture was refluxed for 4 hours with heating, to give rise to a reaction. After the completion of the reaction, the reaction mixture was cooled and dropwise added to a solution of 18.2 g (0.45 moles) of sodium hydroxide dissolved in 300 ml of water. The organic layer was separated, then washed with a saturated aqueous sodium bicarbonate solution and water, and concentrated to obtain 125 g (0.448 mole) of 2-[1-(4-chlorophenyl)ethyl]-4-isopropyl-4-methyl-1,3-oxazol-5-one (yield=99.6%).

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. temperaturewith heating
  3. customto give rise
  4. customto a reaction
  5. customAfter the completion of the reaction
  6. temperaturethe reaction mixture was cooled
  7. customThe organic layer was separated
  8. washwashed with a saturated aqueous sodium bicarbonate solution and water
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2b01ca5069e0446f8188058d196cdf36
Source dataset
uspto-grants-2003_01
Patent number
US06504046B1

Reaction notes

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