Sulfuric Acid → 2-(4-chlorophenyl)-N-[1-methyl-1-isopropyl-2-oxopropyl]propanamide

HRID 1633806Notes

Reaction equation

HRID 1633806 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:23])[C:9]([NH:11][C:12]([CH3:22])([CH:19]([CH3:21])[CH3:20])[C:13](=[O:18])[CH2:14]C([O-])=O)=[O:10])=[CH:4][CH:3]=1.CC(O)C.S(=O)(=O)(O)O.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:23])[C:9]([NH:11][C:12]([CH3:22])([CH:19]([CH3:20])[CH3:21])[C:13](=[O:18])[CH3:14])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 186801994-[2-(4-Chlorophenyl)propanoylamino]-4,5-dimethyl-3-oxohexanoate

Product 1

HCID 114833132-(4-chlorophenyl)-N-[1-methyl-1-isopropyl-2-oxopropyl]propanamideYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

In a reactor were placed 57.5 g (0.156 mole) of 4-[2-(4-chlorophenyl)propanoylamino]-4,5-dimethyl-3-oxohexanoate, 156 ml of 2-propanol, 62.4 ml of water and 15.6 ml of concentrated sulfuric acid. The mixture was refluxed for 7 hours with heating, to give rise to a reaction. After the completion of the reaction, the reaction mixture was cooled to 60° C. 446 ml of water was added for further cooling. The mixture was neutralized with a 23% aqueous sodium hydroxide solution. The precipitated crystals were collected by filtration to obtain 41.5 g (0.14 mole) of 2-(4-chlorophenyl)-N-[1-methyl-1-(methylethyl)-2-oxopropyl]propanamide (yield=90%).

Workup

  1. customIn a reactor were placed
  2. temperatureThe mixture was refluxed for 7 hours
  3. temperaturewith heating
  4. customto give rise
  5. customto a reaction
  6. customAfter the completion of the reaction
  7. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-2a37170aa2794b6f8c40b664924a4756
Source dataset
uspto-grants-2003_01
Patent number
US06504046B1

Reaction notes

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