Benzamide → N-Butylbenzamide

HRID 1638763Notes

Reaction equation

HRID 1638763 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH3:5].[C:6]([NH2:14])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>C1C=CC=CC=1.O>[CH2:2]([NH:14][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 2331BenzamideHCID 8002Butyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 76024N-Butylbenzamide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

1-Bromobutane (1.51 g, 0.011 mol) in benzene (10 ml) was slowly added to a refluxing mixture of benzamide (1.21 g, 0.01 mol), 50% aqueous sodium hydroxide solution (10 ml) and 1 mmol of the catalyst (Table 3). After the addition of has been completed, refluxing is continued for 4 hours. The reaction mixture was then cooled to room temperature and diluted with water (20 ml). The organic phase is separated, washed with water (3×10 ml) until neutral, dried over magnesium sulphate and evaporated to give pure N-n-butylbenzamide. Yields are given in Table 3.

Workup

  1. additionAfter the addition
  2. temperaturerefluxing
  3. customThe organic phase is separated
  4. washwashed with water (3×10 ml) until neutral,
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-1517a2593f0c42d8aff2f9b3ccadd983
Source dataset
uspto-grants-1989_11
Patent number
US04880894

Reaction notes

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