Pentane → HCID 13784988, compound

HRID 980243Notes

Reaction equation

HRID 980243 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([NH2:6])=[O:5].C(Cl)(=O)[C:13](Cl)=[O:14].[NH2:18][C:19]1[CH:20]=[CH:21][C:22]2[O:26][C:25]([F:28])([F:27])[C:24]([F:30])([F:29])[C:23]=2[CH:31]=1.CCCCC>C1(C)C=CC=CC=1>[F:28][C:25]1([F:27])[C:24]([F:30])([F:29])[C:23]2[CH:31]=[C:19]([NH:18][C:13]([NH:6][C:4](=[O:5])[C:3]3[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=3[F:11])=[O:14])[CH:20]=[CH:21][C:22]=2[O:26]1

Participants

6

Reactant 4

HCID 8003PentaneHCID 65578Oxalyl chlorideHCID 874392,6-DifluorobenzamideHCID 137849875-Benzofuranamine, 2,2,3,3-tetrafluoro-2,3-dihydro-

Product 1

HCID 13784988HCID 13784988, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

Under a dry nitrogen atmosphere a mixture of 0.55 g (0.0035 mole) 2,6-difluorobenzamide, 0.48 g (0.0038 mole) oxalyl chloride, and 70 ml of toluene was heated at reflux for two hours. The mixture was cooled and distilled under reduced pressure to remove excess oxalyl chloride and approximately 60 ml of toluene. To the pot residue were added 30 ml of fresh toluene and 0.72 g (0.0035 mole) 5-amino-2,2,3,3-tetrafluoro-2,3-dihydrobenzofuran dissolved in 30 ml of toluene. The resultant mixture was allowed to stir at room temperature for approximately 18 hours. Approximately 100 ml of n-pentane was added to this mixture. A white precipitate formed after stirring for an additional hour. This solid was collected by filtration to yield 0.74 g of N-[[(2,2,3,3-tetrafluoro-2,3-dihydrobenzofuran-5-yl)amino]carbonyl]-2,6-difluorobenzamide (mp 183°-184.5° C.), Compound 1 of Table 1. The nmr and ir spectra were consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for two hours
  3. temperatureThe mixture was cooled
  4. distillationdistilled under reduced pressure
  5. customto remove excess oxalyl chloride and approximately 60 ml of toluene
  6. customA white precipitate formed
  7. stirringafter stirring for an additional hour
  8. filtrationThis solid was collected by filtration

Sources & evidence

ORD record
ord-afdd0d987c544f08ac3a78feb06ee5c1
Source dataset
uspto-grants-1987_01
Patent number
US04636523

Reaction notes

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