4-Butylaniline → Acetamide, N-(4-butylphenyl)-

HRID 1925711Notes

Reaction equation

HRID 1925711 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(N(CC)CC)C.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:19](=[O:21])[CH3:20])=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 76944-ButylanilineHCID 7918Acetic AnhydrideHCID 8471Triethylamine

Product 1

HCID 77227Acetamide, N-(4-butylphenyl)-Yield 58.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

To 4-butyl aniline (20 g; 134 mmol) dissolved in toluene (160 mL) with stirring was added 4-dimethylaminopyridine (0.82 g; 6.70 mmol) and triethylamine (26.0 mL; 188 mmol). The mixture was then treated with acetic anhydride (15.2 mL; 161 mmol) dropwise via an addition funnel over 30 minutes. After addition, the ice bath was removed and the reaction mixture was stirred for 12 hours at room temperature. The mixture was poured into aqueous hydrochloric acid (240 mL; 2M) and stirred 20 minutes. The layers were separated and the organic layer was washed with water. The organic layer was separated and crystals formed while standing. The resulting precipitate was isolated by filtration and dried under vacuum to give the title product as white crystals (15.0 g).

Workup

  1. additionAfter addition
  2. customthe ice bath was removed
  3. stirringthe reaction mixture was stirred for 12 hours at room temperature
  4. additionThe mixture was poured into aqueous hydrochloric acid (240 mL; 2M)
  5. stirringstirred 20 minutes
  6. customThe layers were separated
  7. washthe organic layer was washed with water
  8. customThe organic layer was separated
  9. customcrystals formed
  10. customThe resulting precipitate was isolated by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-8c0562014fdd42aabafce7fa6f517e0c
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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