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

HRID 2259262Notes

Reaction equation

[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[N+:6]([C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1)([O-:8])=[O:7]>>[C:1]([NH:5][C:13](=[O:14])[C:12]1[CH:11]=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:17][CH:16]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 6385Tert-Butylamine

HCID 85024-Nitrobenzoyl chloride

Product 1

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

Procedure

The preparation of Example 1 was repeated with the changes that tert-butyl amine (14.6 g, 0.200 mole) and 4-nitrobenzoyl chloride (18.6 g, 0.100 mole) were the starting reactants. This reaction produced 17.13 g of crystals of the desired product (77% yield), mp 162°-163° C. proton nuclear magnetic resonance (89.55 MHz) showed absorptions at 8.257 ppm (d, 8.8 Hz, 2H; 3,5-aryl H); 7.878 ppm (d, 8.8 Hz, 2H; 2,6-aryl H); 6.097 ppm (bs, 1H; N-H); 1,500 ppm (s, 9H; tert-butyl H).

Workup

customThe preparation of Example 1

Sources & evidence

ORD record: ord-d5a4b96c22c546fcb9cf020e91142f04
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05472983

Reaction notes

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