Benzyl Alcohol → HCID 67954029, compound

HRID 2402551Notes

Reaction equation

HRID 2402551 reaction equation
[CH2:1]([NH2:3])[CH3:2].F[C:5]1[CH:10]=[C:9](F)[CH:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13].[CH2:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.C1(C)C=CC=CC=1>[CH2:15]([O:22][C:9]1[CH:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]([CH:10]=1)[NH:3][CH2:1][CH3:2])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 6341EthylamineHCID 11430Potassium CarbonateHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 67954029HCID 67954029, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent3×HCID 1140TolueneSolvent2×

Conditions

Temperature
37.5 °C

Procedure

An aqueous solution of 70% ethyl amine (25 mL, 0.315 mol) was added dropwise to a toluene solution (167 mL) of 2,4-difluoronitrobenzene (16.7 g, 0.105 mol) under ice cooling, and the mixture was stirred at 35-40° C. for 2 hours. Water was added to the reaction solution, and toluene extraction was performed, followed by washing with water. The resulting organic layer was concentrated under reduced pressure until reduced to about half (the concentrated solution including a crude product of 5-fluoro-N-ethyl-2-nitroaniline). Benzyl alcohol (21.7 mL, 0.21 mol), tetrabutyl ammonium hydrogen sulfate (3.56 g, 0.01 mmol), potassium carbonate (21.76 g, 0.157 mol), and water (1.7 mL) were added to the resulting solution, and the mixture was heated under reflux for 3 hours. The reaction solution was cooled, and water (84 mL) was added thereto. Thereafter, the mixture was stirred at 70° C. for 1 hour, and stirred under ice cooling for 30 minutes. Next, precipitated crystals were collected by filtration, and the resulting crystals were washed with water, and dried at 50° C., thereby obtaining 17.7 g of a yellow, powdery target compound (yield: 62%).

Workup

  1. washby washing with water
  2. concentrationThe resulting organic layer was concentrated under reduced pressure
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 3 hours
  5. temperatureThe reaction solution was cooled
  6. stirringThereafter, the mixture was stirred at 70° C. for 1 hour
  7. stirringstirred under ice cooling for 30 minutes
  8. customNext, precipitated crystals
  9. filtrationwere collected by filtration
  10. washthe resulting crystals were washed with water
  11. customdried at 50° C.

Sources & evidence

ORD record
ord-a5f70d8251944d1c82d6a5be918a7226
Source dataset
uspto-grants-2014_08
Patent number
US08796447B2

Reaction notes

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