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

HRID 583017Notes

Reaction equation

HRID 583017 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) with pyridine (140 ml) in a nitrogen atmosphere. To the solution, octadecanoyl chloride (333 g) was added through the dropping funnel over a time span of 20 minutes, while stirring the reaction mixture. After the completion of the dropwise addition, the reaction mixture was stirred for 2 hours. The resultant solid product was removed by filtering, and the filtrate was concentrated under reduced pressure, to produce crystals. The crystals were collected and recrystallized from ethanol. 4'-nitro-n-octadecaneanilide (364 g) was obtained at a yield of 90%.

Workup

  1. customIn a three necked flask equipped with a dropping funnel
  2. additionAfter the completion of the dropwise addition
  3. stirringthe reaction mixture was stirred for 2 hours
  4. customThe resultant solid product was removed
  5. filtrationby filtering
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customto produce crystals
  8. customThe crystals were collected
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5486eabbc2874a3c9414edc645870a99
Source dataset
uspto-grants-1999_07
Patent number
US05928988

Reaction notes

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