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

HRID 2259265Notes

Reaction equation

HRID 2259265 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[CH3:6][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]([CH3:6])=[CH:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 134054-Methylbenzoyl Chloride

Product 1

HCID 576940N-tert-Butyl-4-methylbenzamideYield 89%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The preparation of Example 1 was repeated with the changes that the starting reactants were tert-butyl amine (4.72 g, 0.065 mole) and 4-methylbenzoyl chloride (5.02 g, 0.0325 mole), the reaction was carried out in benzene and the reaction produced 5.54 g of crystals of the desired product (89% yield), mp 114°-116° C. Proton nuclear magnetic resonance (89.55 MHz) showed absorptions at 7.615 ppm (d, 8 Hz, 2H; 2,6-aryl H); 7.193 ppm (d, 8 Hz, 2H; 3.5-aryl H); 5.970 ppm (bs, 1H; N-H); 2.377 ppm (s, 3H; 4-CH3); 1.461 ppm (s, 9H; tert-butyl H).

Workup

  1. customThe preparation of Example 1

Sources & evidence

ORD record
ord-89e462aaeb1f494898bf5041cd2ed561
Source dataset
uspto-grants-1995_12
Patent number
US05472983

Reaction notes

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