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

HRID 2259263Notes

Reaction equation

HRID 2259263 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>C1C=CC=CC=1>[C:1]([NH:5][C:11](=[O:12])[C:10]1[CH:14]=[CH:15][C:7]([Br:6])=[CH:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 6032584-bromo-N-tert-butylbenzamideYield 89%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The preparation of Example 1 was repeated with the changes that tert-butyl amine (4.02 g, 0.055 mole) and 4-bromobenzoyl chloride (6.04 g, 0.0275 mole) were the starting reactants and benzene was the reaction medium. This reaction produced 6.24 g crystals (89% yield), mp 130°-133° C. Proton nuclear magnetic resonance (89.55 MHz) showed absorptions at 7.562 ppm (s, 4H; aryl H); 5.910 ppm (bs, 1H; N-H); 1.464 ppm (s, 9H; tert-butyl H).

Workup

  1. customThe preparation of Example 1

Sources & evidence

ORD record
ord-ed9a7e7125504a419ad0ebc4531f49be
Source dataset
uspto-grants-1995_12
Patent number
US05472983

Reaction notes

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