Aniline → Acetamide, N-(3,5-dimethylphenyl)-

HRID 1519004Notes

Reaction equation

HRID 1519004 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH3:8][C:9]1[CH:10]=[C:11]([CH:13]=[C:14]([CH3:16])[CH:15]=1)[NH2:12].NC1C=CC=CC=1.[OH-].[Na+]>C1COCC1>[CH3:8][C:9]1[CH:10]=[C:11]([NH:12][C:5](=[O:7])[CH3:6])[CH:13]=[C:14]([CH3:16])[CH:15]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 7918Acetic AnhydrideHCID 79493,5-DimethylanilineHCID 14798Sodium Hydroxide

Product 1

HCID 74903Acetamide, N-(3,5-dimethylphenyl)-Yield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic anhydride (2.84 mL, 30 mmol) was dissolved in dry THF (10 mL), purged with N2 and brought to 0° C. 3,5-Dimethylaniline (1.25 mL, 10 mmol) was then added dropwise. After the addition of the aniline, the reaction was allowed to warm to room temperature and stirred for an additional hour. The solution was then poured over ice and 1 M NaOH (aq) was added until the pH was between 12 and 14. The precipitate was filtered, dissolved in DCM and dried over Na2SO4. The drying agent was filtered and solvent was removed under reduced pressure to afford pure product in 99% yield as a white solid.

Workup

  1. custompurged with N2
  2. custombrought to 0° C
  3. additionwas added until the pH was between 12 and 14
  4. filtrationThe precipitate was filtered
  5. dissolutiondissolved in DCM
  6. dry with materialdried over Na2SO4
  7. filtrationThe drying agent was filtered
  8. customsolvent was removed under reduced pressure
  9. customto afford pure product in 99% yield as a white solid

Sources & evidence

ORD record
ord-cbe79b07ee7043039835b7fd89026fba
Source dataset
uspto-grants-2015_07
Patent number
US09073863B2

Reaction notes

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