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

HRID 2188497Notes

Reaction equation

HRID 2188497 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]([NH2:17])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C>C(Cl)Cl>[C:13]([NH:17][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Nitrobenzoyl chloride (18.9 g, 0.1 mol) dissolved in 60 ml of methylene chloride is added, over 30 minutes at a temperature of 0-5° C., to a solution of tert-butylamine (8.3 g, 0.112 mol) and of triethylamine (15.6 ml, 0.112 mol) dissolved in 170 ml of dichloromethane in a reactor. The reaction mixture is brought back to laboratory temperature and left stirring for 2 hours. The organic phase is washed twice with water and dried. After removing the solvent under reduced pressure, the solid obtained is recrystallized from isopropanol. 17.1 g (Yield: 77%) of N-(tert-butyl)-4-nitrobenzamide are obtained in the form of a pale yellow powder (m.p. 161-2° C.) which is used as is in the following stage.

Workup

  1. waitleft
  2. washThe organic phase is washed twice with water
  3. customdried
  4. customAfter removing the solvent under reduced pressure
  5. customthe solid obtained
  6. customis recrystallized from isopropanol

Sources & evidence

ORD record
ord-c7e6f35aea7e4ab5b69cb40d3555966a
Source dataset
uspto-grants-2012_12
Patent number
US08323624B2

Reaction notes

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