Water → N-(2,6-dimethoxy-4-methylphenyl)isovaleramide

HRID 2922

Reaction equation

HRID 2922 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([O:11][CH3:12])[C:4]=1[NH2:5].C(N(CC)CC)C.[C:20](Cl)(=[O:25])[CH2:21][CH:22]([CH3:24])[CH3:23].O>C(OCC)C>[CH3:12][O:11][C:6]1[CH:7]=[C:8]([CH3:10])[CH:9]=[C:3]([O:2][CH3:1])[C:4]=1[NH:5][C:20](=[O:25])[CH2:21][CH:22]([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 66054Isovaleryl chlorideHCID 124090902,6-Dimethoxy-4-methylaniline

Product 1

HCID 18936492N-(2,6-dimethoxy-4-methylphenyl)isovaleramideYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

8.2 g of 2,6-dimethoxy-4-methylaniline are dissolved in 100 ml of diethyl ether at 0° C. under an inert atmosphere, 5.96 g of triethylamine are added to the reaction mixture and then 6.51 g of isovaleryl chloride are added dropwise, while maintaining the temperature at 0° C. The mixture is left at room temperature for 30 minutes and is then poured into 250 ml of water. The aqueous phase is extracted with ethyl acetate after separation by settling of the ethereal phase. The organic phases are combined and washed with water, then dried over anhydrous sodium sulphate and evaporated to dryness. The white crystals of N-(2,6-dimethoxy-4-methylphenyl)isovaleramide obtained are washed with diisopropyl ether; M.p.=139° C., Yield: 92%.

Workup

  1. additionare added to the reaction mixture
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. customafter separation
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-008f672ce81f498d931758715cd6380b
Source dataset
uspto-grants-1998_03
Patent number
US05731340

Linked notes

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