Pyridine → 2-(2-Fluoroacetamido)-N-(2-methylphenyl)-5-nitrobenzamide

HRID 1658722Notes

Reaction equation

HRID 1658722 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[C:8]([CH3:13])=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:5].N1C=CC=CC=1.[F:27][CH2:28][C:29](Cl)=[O:30]>O1CCCC1>[F:27][CH2:28][C:29]([NH:1][C:2]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[C:8]([CH3:13])=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:5])=[O:30]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9663Fluoroacetyl chlorideHCID 124873692-Amino-N-(2-methylphenyl)-5-nitrobenzamide

Product 1

HCID 215254582-(2-Fluoroacetamido)-N-(2-methylphenyl)-5-nitrobenzamideYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

14.4 g(0.053 mol) of N-(2-amino-5-nitrobenzoyl)-o-toluidine and 6.3 g(0.08 mol) of pyridine are dissolved in 300 ml of tetrahydrofuran. 12.2 g(0.126 mol) of fluoroacetyl chloride are added to the solution for 10 minutes under ice-cooling. The solution is stirred at the same temperature for 30 minutes and then at room temperature for 2.5 hours. The reaction solution is allowed to stand at room temperature overnight. The crystalline precipitate is collected by filtration, washed with water and then dried. 16.4 g of N-(2-fluoroacetamido-5-nitrobenzoyl)-o-toluidine are obtained.

Workup

  1. temperaturecooling
  2. waitat room temperature for 2.5 hours
  3. waitto stand at room temperature overnight
  4. filtrationThe crystalline precipitate is collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-8f1f19b74be44caa9ca7c68e4adaf40e
Source dataset
uspto-grants-1976_06
Patent number
US03966731

Reaction notes

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