Tert-Butylamine → N-tert-Butyl-4-nitrobenzamide

HRID 1421522Notes

Reaction equation

HRID 1421522 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[N+:6]([C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1)([O-:8])=[O:7]>C(OCC)(=O)C>[C:1]([NH:5][C:13](=[O:14])[C:12]1[CH:11]=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:17][CH:16]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 591441N-tert-Butyl-4-nitrobenzamideYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

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 4-nitrobenzoyl chloride (18.6 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 the 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 over at 24 mm and 45° C. for 14 hours. The procedure produced 17.13 g of crystals of N-tert-butyl-4-nitrobenzamide (CPI1020) (77% yield), mp 162-163° C. Proton nuclear magnetic resonance (89.55 MHz in CDCl3) showed absorptions at 8.257 ppm (d, 8.8 Hz, 2H; 3,5-aryl H); 7.878 ppm (d, 8.8 Hz, 2H; 2,6-aryl H); 6.097 ppm (bs, 1H; N--H); 1.500 ppm (s, 9H; tert-butyl H).

Workup

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

Sources & evidence

ORD record
ord-c2a5c36af0f04b8592338bfa34aa24fa
Source dataset
uspto-grants-2000_06
Patent number
US06077870

Reaction notes

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