Dinitrofluorobenzene → HCID 4922992, compound

HRID 428798Notes

Reaction equation

HRID 428798 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1F)([O-:3])=[O:2].CN1CCCC1=O.[CH2:21]([NH:24][CH2:25][CH:26]=[CH2:27])[CH:22]=[CH2:23].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:21]([N:24]([CH2:25][CH:26]=[CH2:27])[C:5]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH:22]=[CH2:23]

Participants

6

Reactant 4

HCID 6264DinitrofluorobenzeneHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 31279Diallylamine

Product 1

HCID 4922992HCID 4922992, compoundYield 110.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,4-dinitrofluorobenzene (9.3 g, 50 mmol), 1-methylpyrrolidinone (50 mL), diallylamine (5.82 g, 60 mmol) and potassium carbonate (6.9 g, 50 mmol) was stirred at ambient temperature for 1 h. The mixture was poured into water (250 mL) and extracted with ethyl ether. The ether extract was washed with 0.5 N hydrochloric acid, water, and saturated brine solution, and dried over magnesium sulfate. Concentration of the extract gave N,N-diallyl-2,4-dinitrobenzeneamine as a yellow oil (14.6 g).

Workup

  1. extractionextracted with ethyl ether
  2. extractionThe ether extract
  3. washwas washed with 0.5 N hydrochloric acid, water, and saturated brine solution
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-56ede6ead58046d989ae0aacd33d301f
Source dataset
uspto-grants-2001_11
Patent number
US06313348B1

Reaction notes

Loading…