4-Nitroaniline → N-(4-Nitrophenyl)octadecanamide

HRID 583014Notes

Reaction equation

HRID 583014 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:11](Cl)(=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>O1CCCC1.N1C=CC=CC=1>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:11](=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 74754-NitroanilineHCID 8212Stearoyl chloride

Product 1

HCID 21226385N-(4-Nitrophenyl)octadecanamideYield 90%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a three necked flask equipped with a dropping funnel, a thermometer and a reflux condenser, p-nitroaniline (138 g) was dissolved in a mixed solution of tetrahydrofuran (200 ml) and pyridine (140 ml) in a nitrogen atmosphere. Then, octadecanoyl chloride (333 g) was added dropwise into the three necked flask through the dropping funnel, over a time span of 20 minutes while stirring the reaction mixture. After the completion of the dropping, the reaction mixture was stirred for 2 hours. Then, a solid product was produced. The solid product was filtered and the filtrate was concentrated under a reduced pressure to provide crystals. The crystals were collected and recrystallized from ethanol. 4'-nitro-n-octadecaneanilide (364 g) was obtained. The yield thereof was 90%.

Workup

  1. customIn a three necked flask equipped with a dropping funnel
  2. stirringAfter the completion of the dropping, the reaction mixture was stirred for 2 hours
  3. customThen, a solid product was produced
  4. filtrationThe solid product was filtered
  5. concentrationthe filtrate was concentrated under a reduced pressure
  6. customto provide crystals
  7. customThe crystals were collected
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6405e4356fde4784aed37aa80be79b58
Source dataset
uspto-grants-1999_07
Patent number
US05928988

Reaction notes

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