Water → Acetamide, N-(4-butylphenyl)-

HRID 1684422Notes

Reaction equation

HRID 1684422 reaction equation
[CH2:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[C:12](OC(=O)C)(=[O:14])[CH3:13].O>C(O)(=O)C>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:12](=[O:14])[CH3:13])=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 76944-ButylanilineHCID 7918Acetic Anhydride

Product 1

HCID 77227Acetamide, N-(4-butylphenyl)-Yield 96.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

95.0 g (0.64 mol) of p-normalbutylaniline was dissolved in 170 ml of glacial acetic acid. 81.3 g (0.80 mol) of acetic anhydride was then added dropwise to the solution at a temperature of 30° C. After the completion of dropwise addition, the reaction mixture was then allowed to undergo reaction at a temperature of 40° C. for 1 hour. The reaction solution was then poured into 600 ml of water. The resulting crystal was filtered off, washed with water, and then dried. The crystal thus obtained was then recrystallized from a mixture of 120 ml of toluene and 1,000 ml of n-hexane to obtain 117.5 g (yield: 96.4%) of p-normalbutylacetanilide. The melting point of the crystal was from 105.5° C. to 106.0° C.

Workup

  1. additionAfter the completion of dropwise addition
  2. customreaction at a temperature of 40° C. for 1 hour
  3. filtrationThe resulting crystal was filtered off
  4. washwashed with water
  5. customdried
  6. customThe crystal thus obtained
  7. customwas then recrystallized from a mixture of 120 ml of toluene and 1,000 ml of n-hexane

Sources & evidence

ORD record
ord-b76c351ecdd74674b54eb96086e1795d
Source dataset
uspto-grants-1997_06
Patent number
US05639914

Reaction notes

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