Triethylamine → N-(3-methoxyphenyl)pivalamide

HRID 2061449Notes

Reaction equation

HRID 2061449 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108243-MethoxyanilineHCID 62493Pivaloyl chloride

Product 1

HCID 546358N-(3-methoxyphenyl)pivalamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
15 °C

Procedure

To an ice cooled solution of 20 g (162 mmol) 3-methoxy-phenylamine in 400 ml diethylether is added 24.9 ml (178 mmol) triethylamine and slowly within 30 minutes 23.9 ml (195 mmol) pivaloyl chloride. Due to the exothermic reaction the temperature rises despite cooling to 15° C. The temperature is left rising to room temperature, after 1 hour the reaction mixture is poured on ice and extracted with ethyl acetate, washed 2× with water and 1× with brine, dried with Na2SO4 and evaporated to give a crude product which is purified by two crystallizations from CH2Cl2/hexane to yield N-(3-methoxy-phenyl)-2,2-dimethyl-propionamide.

Workup

  1. customDue to the exothermic reaction the temperature
  2. waitThe temperature is left
  3. additionthe reaction mixture is poured on ice
  4. extractionextracted with ethyl acetate
  5. washwashed 2× with water and 1× with brine
  6. dry with materialdried with Na2SO4
  7. customevaporated
  8. customto give a crude product which
  9. customis purified by two crystallizations from CH2Cl2/hexane

Sources & evidence

ORD record
ord-a0c48113b13e48d88f2b09e1cf8a0b0a
Source dataset
uspto-grants-2012_10
Patent number
US08283356B2

Reaction notes

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