Sodium Hydroxide → N-(3-Bromo-4-methylphenyl)-3-tert-butylbenzamide

HRID 1055663Notes

Reaction equation

HRID 1055663 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[C:10]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17](O)=[O:18])([CH3:13])([CH3:12])[CH3:11].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[OH-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][CH:22]=[C:14]([C:10]([CH3:12])([CH3:11])[CH3:13])[CH:15]=2)[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 82187Benzenamine, 3-bromo-4-methyl-HCID 139037m-tert-Butylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 86690964N-(3-Bromo-4-methylphenyl)-3-tert-butylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

285 mg (1.53 mmol) of 3-bromo-4-methylaniline, 300 mg (1.68 mmol) of 3-tert-butylbenzoic acid and 698 mg (1.83 mmol) of HATU were dissolved in 3 ml of DMF, 0.32 ml (1.83 mmol) of N,N-diisopropylethylamine were added and the mixture was stirred at RT for 16 h. The reaction was then stirred into 20 ml of 0.1 M aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic phase was washed with water and saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure. Drying of the residue gave 490 mg (88% of theory) of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water and saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customDrying of the residue

Sources & evidence

ORD record
ord-908c962ff6e24b09a2e6839495c9a3c3
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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