Triethylamine → HCID 53846798, compound

HRID 2270241Notes

Reaction equation

HRID 2270241 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9](F)[C:8]([F:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:14](Cl)(=O)[C:15](Cl)=O.C([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])C.N1CCCC1>ClCCl.CN(C=O)C.O>[CH2:14]([O:6][C:4](=[O:5])[C:3]1[CH:7]=[C:8]([F:13])[C:9]([N:22]2[CH2:23][CH2:24][CH2:26][CH2:25]2)=[C:10]([F:11])[C:2]=1[F:1])[CH3:15]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 65578Oxalyl chlorideHCID 2975492,3,4,5-Tetrafluorobenzoic acid

Product 1

HCID 53846798HCID 53846798, compoundYield 61.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2,3,4,5-tetrafluorobenzoic acid (5.0 g, 28.7 mmol) in dichloromethane (20 mL) was reacted with oxalyl chloride (7.5 mL, 86.1 mmol) and one drop of DMF. The mixture was stirred for 30 minutes and concentrated. The residue was dissolved in dichloromethane (20 mL) and reacted with an excess of dry ethanol. After 10 minutes, H2O was added and the mixture extracted with diethyl ether. The organic layer was then dried with sodium sulfate and concentrated. The residue was taken up in acetonitrile (100 mL) and reacted with triethylamine (21.0 mL, 150 mmol) and pyrrolidine (3.2 mL, 37 mmol). The reaction was allowed to proceed overnight and was concentrated. The residue was taken up in diethyl ether and washed with saturated NaHCO3. The organic layer was dried with magnesium sulfate and concentrated to provide 4.8 g of the title compound as an oil.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  3. customreacted with an excess of dry ethanol
  4. waitAfter 10 minutes
  5. extractionthe mixture extracted with diethyl ether
  6. dry with materialThe organic layer was then dried with sodium sulfate
  7. concentrationconcentrated
  8. waitto proceed overnight
  9. concentrationwas concentrated
  10. washwashed with saturated NaHCO3
  11. dry with materialThe organic layer was dried with magnesium sulfate
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-50ec7b9ce00f4e94a4703bcdc2a9899e
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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