3-Nitroaniline → HCID 19388966, compound

HRID 1757885Notes

Reaction equation

HRID 1757885 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[CH2:11]([N:29]=[C:30]=[O:31])[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].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][C:30]([NH:29][CH2:11][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])=[O:31])[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 74233-NitroanilineHCID 8471TriethylamineHCID 66988Octadecyl isocyanate

Product 1

HCID 19388966HCID 19388966, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.5 g (3.6 mmol) of 3-nitroaniline, 1.2 mL (3.9 mmol) of octadecyl isocyanate 0.7 mL (5 mmol) of triethylamine and 0.1 mL of 4-dimethylaminopyridine in 30 mL of anhydrous THF was stirred at reflux for 18 hours. The reaction mixture was concentrated at reduced pressure and the residue was recrystallized from THF methanol-water to give 1.3 g of N-(3-nitrophenyl)-N'-octadecylurea.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationThe reaction mixture was concentrated at reduced pressure
  3. customthe residue was recrystallized from THF methanol-water

Sources & evidence

ORD record
ord-d248e5a323b5423186dfe2cd79bf95ad
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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