Sodium Chloride → HCID 22617097, compound

HRID 1493838Notes

Reaction equation

HRID 1493838 reaction equation
[H-].[Na+].P(=O)([O-])O[C:5]([CH2:17][CH3:18])(CC)[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.[CH:21]1[C:31]2C=C[C:28]3[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=3[C:26](=O)[C:25]=2[CH:24]=[CH:23][CH:22]=1.[Na+].[Cl-]>CS(C)=O>[N+:12]([C:9]1[CH:8]=[CH:7][C:6]([CH:5]=[C:17]2[C:18]3[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=3[CH:27]=[CH:26][C:25]3[CH:31]=[CH:21][CH:22]=[CH:23][C:24]2=3)=[CH:11][CH:10]=1)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 166795H-Dibenzo[a,d]cyclohepten-5-oneHCID 24758Sodium hydrideHCID 178447636HCID 178447636, compound

Product 1

HCID 22617097HCID 22617097, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
70 °C

Procedure

150 ml of dimethyl sulfoxide was admixed with 3.60 g (about 90 mmoles) of oily sodium hydride (about 60%) at room temperature. After the addition, the mixture was heated over an oil bath to an inside temperature of about 70° C., and stirred as such for about one hour. Then, the reaction mixture was cooled to room temperature, and a solution of 25.1 g (92 m moles) of the previously obtained diethyl-4-nitrobenzyl phosphonate and 10.0 g (48.5 m moles) of 5H-dibenzo[a,d]cycloheptene-5-on in 50 ml of dimethyl sulfoxide was added thereto dropwise. After the dropwise addition, the mixture was stirred at room temperature for 15 minutes, and then further stirred with heating at an inside temperature of 70° to 80° C. for 2 hours over an oil bath. After the end of reaction, the mixture was cooled to room temperature, poured into about 1 l of an aqueous saturated NaCl solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then the solvent was removed therefrom under reduced pressure. The residue was admixed with methanol, and the thus precipitated crystal was recovered therefrom by filtration. The thus obtained crystal was recrystallized from methanol-acetone solvent mixture, whereby 10.94 g of 5-(4-nitrobenzylidene)-5H-dibenzo[a,d]cycloheptene was obtained (yield: 69.3%). The melting point was 151.5°-152.5° C. The elemental analysis as C22H15NO2 was as follows:

Workup

  1. additionAfter the addition
  2. temperatureThen, the reaction mixture was cooled to room temperature
  3. additionAfter the dropwise addition
  4. stirringthe mixture was stirred at room temperature for 15 minutes
  5. stirringfurther stirred
  6. temperaturewith heating at an inside temperature of 70° to 80° C. for 2 hours over an oil bath
  7. customAfter the end of reaction
  8. temperaturethe mixture was cooled to room temperature
  9. extractionextracted with ethyl acetate
  10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  11. customthe solvent was removed
  12. customthe thus precipitated crystal was recovered
  13. filtrationby filtration
  14. customThe thus obtained crystal was recrystallized from methanol-acetone solvent mixture

Sources & evidence

ORD record
ord-fe51d9dd94fb4a3bbcc5f1a0971c69bd
Source dataset
uspto-grants-1991_06
Patent number
US05024912

Reaction notes

Loading…