Acetic Acid → 2-Methyl-1-(4-methylphenyl)propan-2-amine

HRID 244930Notes

Reaction equation

HRID 244930 reaction equation
ClCC([NH:5][C:6]([CH3:16])([CH3:15])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)=O.NC(N)=S.C(O)(=O)C.[OH-].[Na+]>C(O)C.O>[CH3:16][C:6]([NH2:5])([CH3:15])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 821299072-chloro-N-(2-methyl-1-p-tolylpropan-2-yl)acetamide

Product 1

HCID 1164872-Methyl-1-(4-methylphenyl)propan-2-amineYield 95.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

6.24 g (26.0 mmol) of 2-chloro-N-(2-methyl-1-p-tolylpropan-2-yl)acetamide and 1.98 g (26.0 mmol) of thiourea were dissolved in 50 mL of ethanol, and 10.2 mL of acetic acid was added dropwise at room temperature. After 3 hours of stirring at 85° C. the resulting white suspension was allowed to cool and diluted with 300 mL of water. The reaction solution was basified with 20 wt % aqueous sodium hydroxide and extracted with hexane, and the extract was washed with saturated aqueous sodium chloride. The organic layer was concentrated under reduced pressure to give 4.04 g of the desired product as a yellow green liquid.

Workup

  1. temperatureto cool
  2. extractionextracted with hexane
  3. washthe extract was washed with saturated aqueous sodium chloride
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-52f5f3f1ba75403a96b8ba283fab6ef9
Source dataset
uspto-grants-2014_02
Patent number
US08658686B2

Reaction notes

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