Boron trifluoride etherate → HCID 13376462, compound

HRID 986648Notes

Reaction equation

HRID 986648 reaction equation
[F:1][CH2:2][C:3]([NH:5][C:6]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:7]=1[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=1[CH3:18])=[O:9])=O.B(F)(F)F.CCOCC>C(O)(=O)C>[F:1][CH2:2][C:3]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=2[CH3:18])[C:8](=[O:9])[C:7]2[C:6](=[CH:22][CH:21]=[C:20]([N+:23]([O-:25])=[O:24])[CH:19]=2)[N:5]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 13376455N-(2,4-Dimethylphenyl)-2-(2-fluoroacetamido)-5-nitrobenzamide

Product 1

HCID 13376462HCID 13376462, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.0 g of N-(2-fluoroacetamido-5-nitrobenzoyl)-2,4-dimethylaniline are added to a mixture of 30 ml of acetic acid and 3.5 g of boron trifluoride etherate, and the mixture is stirred under heating at 100° to 105° C. for 30 minutes. The mixture is cooled and concentrated under reduced pressure to remove acetic acid. 50 ml of water are added to the residue, and the mixture is neutralized with potassium carbonate. The mixture is extracted with chloroform, and the extract is washed with water and dried. The chloroform solution is concentrated under reduced pressure to remove solvent. Isopropanol is added to the residue, and crystalline precipitates are collected by filtration. The thus-obtained crystals (3.0 g, M.p. 198°-200° C.) are recrystallized from a mixture of dimethylformamide and ethanol (1:2). 2.6 g of 2-fluoromethyl-3-(2,4-dimethylphenyl)-6-nitro-4(3H)-quinazolinone are obtained as colorless prisms.

Workup

  1. temperatureunder heating at 100° to 105° C. for 30 minutes
  2. temperatureThe mixture is cooled
  3. concentrationconcentrated under reduced pressure
  4. customto remove acetic acid
  5. addition50 ml of water are added to the residue
  6. extractionThe mixture is extracted with chloroform
  7. washthe extract is washed with water
  8. customdried
  9. concentrationThe chloroform solution is concentrated under reduced pressure
  10. customto remove solvent
  11. additionIsopropanol is added to the residue
  12. customcrystalline precipitates
  13. filtrationare collected by filtration
  14. customThe thus-obtained crystals (3.0 g, M.p. 198°-200° C.) are recrystallized from a mixture of dimethylformamide and ethanol (1:2)

Sources & evidence

ORD record
ord-f54607b876304902882ff3970af90296
Source dataset
uspto-grants-1987_12
Patent number
US04714702

Reaction notes

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