Pyridine → N-(2,4-Dimethylphenyl)-2-(2-fluoroacetamido)-5-nitrobenzamide

HRID 986647Notes

Reaction equation

HRID 986647 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[CH3:14])=[O:5].N1C=CC=CC=1.[F:28][CH2:29][C:30](Cl)=[O:31]>O1CCCC1>[F:28][CH2:29][C:30]([NH:1][C:2]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:8]=1[CH3:14])=[O:5])=[O:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9663Fluoroacetyl chlorideHCID 133764472-Amino-N-(2,4-dimethylphenyl)-5-nitrobenzamide

Product 1

HCID 13376455N-(2,4-Dimethylphenyl)-2-(2-fluoroacetamido)-5-nitrobenzamideYield 88.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.0 g of N-(2-amino-5-nitrobenzoyl)-2,4-dimethylaniline and 2.36 g of pyridine are dissolved in 50 ml of tetrahydrofuran, and 2.18 g of fluoracetyl chloride are added dropwise thereto under ice-cooling. The mixture is then stirred at room temperature for 5 hours. The mixture is concentrated under reduced pressure to remove tetrahydrofuran, and 100 ml of water are added to the residue. Crystalline precipitates are collected by filtration and recrystallized from a mixture of dimethylformamide and ethanol (1:2). 4.3 g of N-(2-fluoroacetamido-5-nitrobenzoyl)-2,4-dimethylaniline are obtained as colorless needles.

Workup

  1. temperatureunder ice-cooling
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customto remove tetrahydrofuran, and 100 ml of water
  4. additionare added to the residue
  5. customCrystalline precipitates
  6. filtrationare collected by filtration
  7. customrecrystallized from a mixture of dimethylformamide and ethanol (1:2)

Sources & evidence

ORD record
ord-7e762bc7c49c443ab6791667982ca6d3
Source dataset
uspto-grants-1987_12
Patent number
US04714702

Reaction notes

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