4-Nitroaniline → HCID 21226391, compound

HRID 1941050Notes

Reaction equation

HRID 1941050 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].O1CCCC1.[C:16](Cl)(=[O:38])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>N1C=CC=CC=1>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:16](=[O:38])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 74754-NitroanilineHCID 8028TetrahydrofuranHCID 4104741Docosanoyl chloride

Product 1

HCID 21226391HCID 21226391, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a three necked flask equipped with a dropping funnel, a thermometer and a reflux condenser, 138 g of p-nitroaniline was dissolved in a mixed solvent consisting of 3000 ml of tetrahydrofuran and 140 ml of pyridine while passing nitrogen gas through the flask. Then, 395 g of docosanoylchloride placed in the dropping funnel was gradually dropped into the flask over a time span of 20 minutes, while stirring the reaction mixture. After the completion of the dropping, the reaction mixture was further stirred for 2 hours. A solid reaction product was produced. The solid reaction product was collected by filtering, the filtrate was concentrated under a reduced pressure to produce crystals. The crystals were collected and recrystallized from ethyl alcohol. As a result, 405 g of 4'-nitro-n-docosaneanilide was obtained at a yield of 88%.

Workup

  1. customIn a three necked flask equipped with a dropping funnel
  2. additionwas gradually dropped into the flask over a time span of 20 minutes
  3. stirringAfter the completion of the dropping, the reaction mixture was further stirred for 2 hours
  4. customA solid reaction product
  5. customwas produced
  6. customThe solid reaction product
  7. customwas collected
  8. filtrationby filtering
  9. concentrationthe filtrate was concentrated under a reduced pressure
  10. customto produce crystals
  11. customThe crystals were collected
  12. customrecrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-7161baa9f4a54bdfa32872889d764aed
Source dataset
uspto-grants-1997_12
Patent number
US05702850

Reaction notes

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