Sulfuric Acid → 2-chloro-N-(2-methyl-1-p-tolylpropan-2-yl)acetamide

HRID 244929Notes

Reaction equation

HRID 244929 reaction equation
[CH3:1][C:2](O)([CH3:11])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.[Cl:13][CH2:14][C:15]#[N:16].S(=O)(=O)(O)[OH:18]>C(O)(=O)C>[Cl:13][CH2:14][C:15]([NH:16][C:2]([CH3:11])([CH3:1])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1)=[O:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7856ChloroacetonitrileHCID 88710Benzeneethanol, alpha,alpha,4-trimethyl-

Product 1

HCID 821299072-chloro-N-(2-methyl-1-p-tolylpropan-2-yl)acetamideYield 90.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8.21 g (50 mmol) of 2-methyl-1-p-tolylpropan-2-ol and 12.0 mL of acetic acid were dissolved in 11.3 g (0.15 mol) of chloroacetonitrile, mixed with 12.0 mL (0.15 mol) of sulfuric acid under cooling with ice and stirred at room temperature for 5 hours. The reaction solution was poured into 200 mL of ice-cold water and extracted with diisopropyl ether. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure to give 10.8 g of the desired product as white crystals.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with diisopropyl ether
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e4a0a973348c4ec4a0bd2c0e0c094e57
Source dataset
uspto-grants-2014_02
Patent number
US08658686B2

Reaction notes

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