Boron trifluoride etherate → HCID 13376464, compound

HRID 986651Notes

Reaction equation

HRID 986651 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]([Cl: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]([Cl: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 13376456HCID 13376456, compound

Product 1

HCID 13376464HCID 13376464, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

22.0 g of N-(2-fluoroacetamido-5-nitrobenzoyl)-2-methyl-4-chloroaniline are dissolved in 170 ml of acetic acid, and 20 g of boron trifluoride etherate are added thereto. The mixture is stirred at 95° to 100° C. for 30 minutes. The mixture is cooled and concentrated under reduced pressure to remove acetic acid. Water is added to the residue and the mixture is neutralized with sodium bicarbonate. The mixture is extracted with chloroform, and the extract is washed with water, dried and then concentrated to dryness under reduced pressure. Isopropanol is added to the crystalline residue and the crystals are collected therefrom. The thus-obtained crystals are recrystallized from a mixture of dimethylformamide and ethanol (1:2). 18.5 g of 2-fluoromethyl-3-(2-methyl-4-chlorophenyl)-6-nitro-4(3H)-quinazolinone are obtained as colorless prisms.

Workup

  1. temperatureThe mixture is cooled
  2. concentrationconcentrated under reduced pressure
  3. customto remove acetic acid
  4. additionWater is added to the residue
  5. extractionThe mixture is extracted with chloroform
  6. washthe extract is washed with water
  7. customdried
  8. concentrationconcentrated to dryness under reduced pressure
  9. additionIsopropanol is added to the crystalline residue
  10. customthe crystals are collected
  11. customThe thus-obtained crystals are recrystallized from a mixture of dimethylformamide and ethanol (1:2)

Sources & evidence

ORD record
ord-6e41a3cc9c8547008cc3b7f1937f5d85
Source dataset
uspto-grants-1987_12
Patent number
US04714702

Reaction notes

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