Tert-Butylamine → 4-bromo-N-tert-butylbenzamide

HRID 2259484Notes

Reaction equation

HRID 2259484 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Br:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1>C(Cl)Cl>[Br:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:12])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 6032584-bromo-N-tert-butylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 22.5 l of methylene chloride and 3030 ml of tert-butylamine is cooled to 0° C. Then a solution of 3 kg of 4-bromo-benzoyl chloride in 15 l of methylene chloride is added in portions. The mixture is cooled to 0°-5° C. and then stirred over night at room temperature. The reaction mixture is filtered and the filtrate washed with 5 l of methylene chloride, three times with 5 l of 3N HCl, twice with 4 l of NaHCO3 and twice with 2 l of brine. The organic layer is dried over Na2SO4 and evaporated. The crude crystals are stirred with 8 l of ether for 30 minutes and the mixture is cooled to 0° C. and filtered. Thus 4-bromo-N-tert-butyl-benzamide is obtained in form of white crystals, m.p.133°-134° C.

Workup

  1. temperatureThe mixture is cooled to 0°-5° C.
  2. filtrationThe reaction mixture is filtered
  3. washthe filtrate washed with 5 l of methylene chloride, three times with 5 l of 3N HCl, twice with 4 l of NaHCO3 and twice with 2 l of brine
  4. dry with materialThe organic layer is dried over Na2SO4
  5. customevaporated
  6. stirringThe crude crystals are stirred with 8 l of ether for 30 minutes
  7. temperaturethe mixture is cooled to 0° C.
  8. filtrationfiltered

Sources & evidence

ORD record
ord-7671575298144efdaabcbdc14fd73d0e
Source dataset
uspto-grants-1995_12
Patent number
US05473078

Reaction notes

Loading…