Aniline → Myristanilide

HRID 426669Notes

Reaction equation

[C:1]([OH:16])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C(C)=CC=CC=1>[C:1]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

Conditions

Temperature: 140 °C

Procedure

A three liter flask equipped with a stirrer, theremometer, nitrogen inlet, Barrett trap and condenser was used. Myristic acid (commercially available from Emery Chemicals, 97 percent purity, 685 grams, 3.0 moles), aniline (300 ml., 3.2 moles) and 120 ml xylene were charged to the flask. The mixture was stirred and heated for approximately 61/2 hours at a temperature of from about 170° C.-220° C. The reaction was conducted in a nitrogen atmosphere. The reaction mixture was then cooled to 140° C. and poured into a 4 liter beaker. About 1.8 liters of denatured alcohol were slowly added to the reaction solution. After standing overnight, the slurry of semi-solid myristanilide was collected by filtration. The filter cake was washed thoroughly with two portions of denatured alcohol and then air dried at about 22° C. The resultant white crystalline solid weighed 706 grams and had a melting point of 83.5° C.-84.5° C.

Workup

customA three liter flask equipped with a stirrer
customnitrogen inlet, Barrett trap and condenser was used
temperatureheated for approximately 61/2 hours at a temperature of from about 170° C.-220° C
additionpoured into a 4 liter beaker
filtrationthe slurry of semi-solid myristanilide was collected by filtration
washThe filter cake was washed thoroughly with two portions of denatured alcohol
customair dried at about 22° C

Sources & evidence

ORD record: ord-67706fa12da847ce94877b7863ba6e76
Source dataset: uspto-grants-1979_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04170956

Reaction notes

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