Benzophenone → HCID 10193287, compound

HRID 983877Notes

Reaction equation

HRID 983877 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[C:11]([C:14]#[N:15])[C:12]#[N:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[C:16]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=O)[C:17]1C=CC=CC=1.C([O-])(=O)C.[NH4+:34]>C1(C)C=CC=CC=1>[NH2:13][CH2:12][C:11]1[C:14]([NH2:34])=[N:15][C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:17][C:10]=1[C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 18091Malononitrile, (piperonylidene)-HCID 517165Ammonium Acetate

Product 1

HCID 10193287HCID 10193287, compoundYield 8.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
118 °C

Procedure

2-Benzo[1,3]dioxol-5-ylmethylene-malononitrile (79 mg, 0.4 mmol), benzophenone (48 mg, 0.4 mmol), ammonium acetate (78 mg, 1.2 mmol), and toluene (4 ml) were placed in a reaction vial and shaken overnight at 118° C. Upon cooling and filtration, the solution was evaporated in a vacuum zentrifuge (45° C.) and the residue was purified by automated, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min). The obtained solid (28 mg) was dissolved in THF (1 ml) and added, under an atmosphere of argon, to a cooled (0° C.) suspension of 100 mg of lithium aluminium hydride in 1 ml THF in a reaction vial. The reaction mixture was shaken first for 2 h at r.t. and subsequently for 4 h at 40° C. Upon cooling, water was added carefully and the mixture was filtered. The filtrate was evaporated in a vacuum zentrifuge (45° C.). Purification of the re-dissolved (DMF, 1 ml) residue by automated, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min) gave 11 mg (7%) of the title compound, MS: m/e=320.1 (M+H+), as a solid.

Workup

  1. temperatureUpon cooling
  2. filtrationfiltration
  3. customthe solution was evaporated in a vacuum zentrifuge (45° C.)
  4. customthe residue was purified by automated, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min)
  5. dissolutionThe obtained solid (28 mg) was dissolved in THF (1 ml)
  6. additionadded, under an atmosphere of argon
  7. temperatureto a cooled
  8. addition(0° C.) suspension of 100 mg of lithium aluminium hydride in 1 ml THF in a reaction vial
  9. stirringThe reaction mixture was shaken first for 2 h at r.t. and subsequently for 4 h at 40° C
  10. temperatureUpon cooling
  11. additionwater was added carefully
  12. filtrationthe mixture was filtered
  13. customThe filtrate was evaporated in a vacuum zentrifuge (45° C.)
  14. customPurification of the
  15. dissolutionre-dissolved (DMF, 1 ml) residue by automated, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min)

Sources & evidence

ORD record
ord-3c0a4e422b164405bfe5545725aa6d25
Source dataset
uspto-grants-2005_03
Patent number
US06867205B2

Reaction notes

Loading…