Aniline → HCID 70452577, compound

HRID 65451Notes

Reaction equation

HRID 65451 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:8][C:9]1[C:14]([C:15]#[N:16])=[C:13]([F:17])[C:12]([C:18]#[N:19])=[C:11]([F:20])[C:10]=1F.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(#N)C>[NH:1]([C:11]1([F:20])[CH:10]=[C:9]([F:8])[C:14]([C:15]#[N:16])=[C:13]([F:17])[CH:12]1[C:18]#[N:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 608182Tetrafluoroisophthalonitrile

Product 1

HCID 70452577HCID 70452577, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 0.85 g of aniline in 20 ml of acetonitrile was dropwise added, while stirring, to a solution of 2.0 g of tetrafluoroisophthalonitrile and 2.0 g of triethylamine in 30 ml of acetonitrile. After dropwise adding, the mixture was stirred at room temperature for 1 hour and an aqueous sodium bicarbonate solution was then added. The mixture was extracted with chloroform and the chloroform extract was washed 5 times with an aqueous sodium chloride solution. After drying with magnesium sulfate, the chloroform was distilled off. The resultant crude crystal was purified by silica gel chromatography (solvent:hexane). Thus, 2.3 g (87% yield) of the desired compound No. 6 was obtained.

Workup

  1. additionAfter dropwise adding
  2. extractionThe mixture was extracted with chloroform
  3. extractionthe chloroform extract
  4. washwas washed 5 times with an aqueous sodium chloride solution
  5. dry with materialAfter drying with magnesium sulfate
  6. distillationthe chloroform was distilled off
  7. customThe resultant crude crystal was purified by silica gel chromatography (solvent:hexane)

Sources & evidence

ORD record
ord-cc6b7dbb434043b799a779764f134485
Source dataset
uspto-grants-1986_09
Patent number
US04614742

Reaction notes

Loading…