4-Nitrobenzoyl chloride → N-tert-butyl-N-methyl-4-nitrobenzamide

HRID 2259266Notes

Reaction equation

HRID 2259266 reaction equation
[C:1]([NH:5][CH3:6])([CH3:4])([CH3:3])[CH3:2].[N+:7]([C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1)([O-:9])=[O:8]>C1C=CC=CC=1>[C:1]([N:5]([CH3:6])[C:14](=[O:15])[C:13]1[CH:17]=[CH:18][C:10]([N+:7]([O-:9])=[O:8])=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 84552N-Methyl-tert-butylamine

Product 1

HCID 591780N-tert-butyl-N-methyl-4-nitrobenzamideYield 72.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The preparation of Example 1 was repeated with the changes that the starting reactants were N-tert-butyl-N-methyl amine (3.36 g, 0.0386 mole) and 4-nitrobenzoyl chloride (3.58 g, 0.0193 mole), the reaction was carried out in benzene, the product was crystallized from cold ethanol, and the desired product was 3.31 g of crystals (28% yield), mp 119°-121° C. Proton nuclear magnetic resonance (89.55 MHz) showed absorptions at 8.252 ppm (d, 8.8 Hz, 2H; 3,5-aryl H); 7.569 ppm (d, 8.8 Hz, 2H; 2,6-aryl H); 2.838 ppm (s, 3H; N-CH3); 1.526 ppm (s, 9H; tert-butyl H) .

Workup

  1. customThe preparation of Example 1
  2. customthe product was crystallized from cold ethanol

Sources & evidence

ORD record
ord-7cb22e0e371c440d96435c1347210660
Source dataset
uspto-grants-1995_12
Patent number
US05472983

Reaction notes

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