3-Nitroaniline → HCID 4338554, compound

HRID 1757801Notes

Reaction equation

HRID 1757801 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].C(N(CC)CC)C.[C:18](Cl)(=[O:36])[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][CH3:35]>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][C:18](=[O:36])[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][CH3:35])[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 74233-NitroanilineHCID 8212Stearoyl chlorideHCID 8471Triethylamine

Product 1

HCID 4338554HCID 4338554, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 2.0 g (14.5 mmol) of 3-nitroaniline and 4.5 ml (32 mmol) of triethylamine in 60 ml of methylene chloride stirred at room temperature was added 5.4 ml (16 mmol) of octadecanoyl chloride in 10 ml of methylene chloride. The reaction mixture was kept at room temperature for 18 hours and then was washed with 1N HCl, dried and concentrated at reduced pressure to a solid. Recrystallization from methanol gave 5.6 g (95% yield, mp 75°-76°) of N-(3-nitrophenyl) octadecanamide.

Workup

  1. washwas washed with 1N HCl
  2. customdried
  3. concentrationconcentrated at reduced pressure to a solid
  4. customRecrystallization from methanol

Sources & evidence

ORD record
ord-7499ebbe9ce34a01b3dd91d89e78d557
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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