Dichloromethane → HCID 15240643, compound

HRID 1654620Notes

Reaction equation

HRID 1654620 reaction equation
ClCCl.[CH3:4][C:5]([NH:15][CH:16]([CH3:20])[C:17](=O)[CH3:18])([C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([Cl:14])[CH:8]=1)[CH3:6].[F:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][C:29](Cl)=[O:30].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[CH3:6][C:5]([N:15]1[CH:16]([CH3:20])[C:17]([CH3:18])=[C:28]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[F:21])[C:29]1=[O:30])([C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([Cl:14])[CH:8]=1)[CH3:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 140040112-(2-Fluorophenyl)acetyl chlorideHCID 15240642HCID 15240642, compound

Product 1

HCID 15240643HCID 15240643, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 20 ml of dichloromethane were added 3.0 g of N-[1-methyl-1-(3-chloro-5-fluorophenyl)ethyl]-N-(1-methyl-2-oxopropyl)amine and 3.5 g of pyridine, and 3.0 g of (2-fluorophenyl)acetyl chloride was then added dropwise thereto at 5° to 10° C. After stirring at room temperature for 1 hour, a saturated aqueous sodium hydrogencarbonate solution was added, followed by extraction with dichloromethane. After dried over anhydrous sodium sulfate, the solution was concentrated by evaporation, and the resulting oil was dissolved in 20 ml of ethyl acetate. Next, 10 ml of a 28% methanol solution of sodium methylate was added thereto, and after stirring under reflux for 15 minutes, the temperature of the solution was returned to room temperature and water was then added, followed by extraction with ethyl acetate. Afterward, the solution was washed with 12% hydrochloric acid and a saturated aqueous solution of sodium hydrogencarbonate, and then dried over anhydrous sodium sulfate. Next, the solution was condensed by an evaporator, and then subjected to silica gel chromatography to obtain 2.2 g of 1-[1-methyl-1-(3-chloro-5-fluorophenyl)ethyl]-4,5-dimethyl-3-(2-fluorophenyl)-3-pyrroline-2-one.

Workup

  1. additionwas then added dropwise
  2. customat 5° to 10° C
  3. extractionfollowed by extraction with dichloromethane
  4. dry with materialAfter dried over anhydrous sodium sulfate
  5. concentrationthe solution was concentrated by evaporation
  6. dissolutionthe resulting oil was dissolved in 20 ml of ethyl acetate
  7. additionNext, 10 ml of a 28% methanol solution of sodium methylate was added
  8. stirringafter stirring
  9. temperatureunder reflux for 15 minutes
  10. customwas returned to room temperature
  11. additionwater was then added
  12. extractionfollowed by extraction with ethyl acetate
  13. washAfterward, the solution was washed with 12% hydrochloric acid
  14. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, and then dried over anhydrous sodium sulfate
  15. customcondensed
  16. customby an evaporator

Sources & evidence

ORD record
ord-8e10510e712c448fb908fa50a03bcc3d
Source dataset
uspto-grants-1995_04
Patent number
US05409886

Reaction notes

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