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

HRID 1292248Notes

Reaction equation

HRID 1292248 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×

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. 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 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 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. 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-d795842aa14e46a0ab5ded601378f785
Source dataset
uspto-grants-1998_05
Patent number
US05756548

Reaction notes

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