Water → N-(4-Methoxy-2-methylphenyl)-2,2-dimethylpropanamide

HRID 2121869Notes

Reaction equation

HRID 2121869 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([CH3:10])[CH:4]=1.C(N(CC)CC)C.[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20].O>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[C:5]([CH3:10])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 76102-Methyl-4-methoxyanilineHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 1

HCID 15414709N-(4-Methoxy-2-methylphenyl)-2,2-dimethylpropanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 4-methoxy-2-methylphenylamine (15.0 g, 109 mmol) and triethylamine (13.3 g, 131 mmol) in anhydrous THF (350 mL) at 0° C. was added pivaloyl chloride (14.1 mL, 13.8 g, 114 mmol). A white precipitate formed and the suspension was stirred for additional 30 min before water (10 mL) was added. The mixture was stirred for 30 min, THF evaporated and the residue was mixed with a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined extracts were dried (MgSO4), filtered and evaporated to an oil (23.5 g, 97%): LC/MS (+APCI) m/z 222 (M+H).

Workup

  1. customA white precipitate formed
  2. additionwas added
  3. customTHF evaporated
  4. additionthe residue was mixed with a saturated aqueous sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to an oil (23.5 g, 97%)

Sources & evidence

ORD record
ord-fc3df86c67c84da5849b6f8594788ed7
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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