Aniline → Pivalanilide

HRID 2259267Notes

Reaction equation

HRID 2259267 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]([CH3:14])([CH3:13])[C:10](Cl)=[O:11]>C1C=CC=CC=1>[C:2]1([NH:1][C:10](=[O:11])[C:9]([CH3:14])([CH3:13])[CH3:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 62493Pivaloyl chloride

Product 1

HCID 81103PivalanilideYield 60%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The preparation of Example 1 was repeated with the changes that the starting reactants were aniline (24.18 g, 0.260 mole) and trimethylacetoyl chloride (15.06 g, 0.125 mole), the reaction was carried out in benzene and produced 13.24 g of crystals of the desired product (60% yield), mp 132°-132.5° C. Proton nuclear magnetic resonance (89.55 MHz) showed absorptions at 7.568-7.078 ppm (m, 5H; aryl H); 1.310 ppm (s, 9H; tert-butyl H).

Workup

  1. customThe preparation of Example 1

Sources & evidence

ORD record
ord-1988c30a6cc04e63802fc6e7ba058298
Source dataset
uspto-grants-1995_12
Patent number
US05472983

Reaction notes

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