Triethyloxonium tetrafluoroborate → HCID 12834621, compound

HRID 1447097Notes

Reaction equation

HRID 1447097 reaction equation
[C:1]1([C:7]2[NH:13][CH2:12][CH2:11][NH:10][C:9](=[O:14])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[B-](F)(F)F.[CH2:20]([O+](CC)CC)[CH3:21]>C(Cl)Cl>[CH2:20]([O:14][C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:13][CH2:12][CH2:11][N:10]=1)[CH3:21]

Participants

4

Reactant 2

HCID 2723982Triethyloxonium tetrafluoroborateHCID 128346207-Phenyl-1,2,3,4-tetrahydro-5H-1,4-diazepin-5-one2×

Product 1

HCID 12834621HCID 12834621, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.8 g. (20 mmol.) of 7-phenyl-1,2,3,4-tetrahydro-1,4-diazepine-5-one (Compound XXV) were suspended in 100 ml. of dry methylene chloride stirred under nitrogen at room temperature. 4.0 g. (21 mmol.) of triethyloxonium tetrafluoroborate were added portionwise to the stirred suspension so as to maintain the reaction mixture at a temperature of 20°-25° C., the reaction being slightly exothermic. After the addition was completed, the reaction mixture was stirred for an additional 30 minutes at room temperature. The reaction mixture was then washed with cold dilute sodium hydroxide solution and dried over anhydrous sodium sulfate. The methylene chloride was evaporated off at reduced pressure and ether was added to the residue. A small amount of solid that did not dissolve was removed by filtration, and the filtrate was evaporated at reduced pressure to yield an oil which crystallized overnight in a refrigerator yielding the crude product (3.5 g.), m.p. 89°-93.5° C. Recrystallization from ether/heptane yielded the pure product as white crystals (1.6 g.), m.p. 94°-95.5° C. A second crop (1.6 g.) was obtained from the mother liquor, m.p. 89°-93° C.

Workup

  1. temperatureto maintain the reaction mixture at a temperature of 20°-25° C.
  2. additionAfter the addition
  3. washThe reaction mixture was then washed with cold dilute sodium hydroxide solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe methylene chloride was evaporated off at reduced pressure and ether
  6. additionwas added to the residue
  7. dissolutionA small amount of solid that did not dissolve
  8. customwas removed by filtration
  9. customthe filtrate was evaporated at reduced pressure
  10. customto yield an oil which
  11. customcrystallized overnight in a refrigerator
  12. customyielding the crude product (3.5 g.), m.p. 89°-93.5° C
  13. customRecrystallization from ether/heptane

Sources & evidence

ORD record
ord-87351c58170b4176873b6b3f0b723572
Source dataset
uspto-grants-1982_02
Patent number
US04315860

Reaction notes

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