Tert-Butylamine → N-t-Butylbenzamide

HRID 2259261Notes

Reaction equation

HRID 2259261 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[C:6](Cl)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(OCC)(=O)C>[C:1]([NH:5][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 7412Benzoyl chloride

Product 1

HCID 138622N-t-ButylbenzamideYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
5 °C

Procedure

tert-Butyl amine (14.6 g, 0.200 mole) was stirred in ethyl acetate (150 mL, purified by washing with 5% sodium carbonate solution, saturated sodium chloride solution, drying over anhydrous magnesium sulfate, and filtering through fluted filter paper) and cooled to 5° C. with an ice bath. Benzoyl chloride (14.0 g, 0.100 mole) in purified ethyl acetate (75 mL) was added dropwise at such a rate to maintain the temperature below 10° C. The ice bath was removed upon complete addition of benzoyl chloride solution and the reaction stirred for 4 hours. The reaction mixture was then filtered on a Buchner funnel, the filtrate washed three times with 5% HCl, once with saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered through fluted filter paper, and the solvent stripped off leaving white crystalline product. The product was dried in a vacuum oven at 24 mm and 45° C. for 14 hours. This procedure produced 15.46 g of crystals of the desired product N-tert-butyl benzamide (CPI1010) (87% yield), mp 133°-135° C. Proton nuclear magnetic resonance (89.55 MHz) showed absorptions at 7.75 ppm (m, 2H; 2,6-aryl H); 7.45 ppm (m, 3H; 3,4,5-aryl H); 5.97 ppm (bs, 1H; N-H); 1.471 ppm (s, 9H, tert-butyl H).

Workup

  1. temperatureto maintain the temperature below 10° C
  2. customThe ice bath was removed upon complete addition of benzoyl chloride solution
  3. filtrationThe reaction mixture was then filtered on a Buchner funnel
  4. washthe filtrate washed three times with 5% HCl
  5. dry with materialonce with saturated sodium chloride, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. filtrationthrough fluted filter paper
  8. customleaving white crystalline product
  9. customThe product was dried in a vacuum oven at 24 mm and 45° C. for 14 hours

Sources & evidence

ORD record
ord-64a62f2fa42b44eab4777a39b6d2d984
Source dataset
uspto-grants-1995_12
Patent number
US05472983

Reaction notes

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