Dimethyl Sulfate → 1-Methyl-2-phenyl-3-oxo-4-(-3-trifluoromethylphenyl)-5-methylamino-4-pyrroline

HRID 236244Notes

Reaction equation

HRID 236244 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:4](=[O:18])[CH:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+].S(OC)(O[CH3:31])(=O)=O.C([N+](CC)(CC)CC)C1C=CC=CC=1>O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[CH3:1][N:2]1[C:6]([NH:7][CH3:31])=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:16])([F:17])[F:15])[CH:9]=2)[C:4](=[O:18])[CH:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 17208BenzyltriethylammoniumHCID 178481250HCID 178481250, compound

Product 1

HCID 138523621-Methyl-2-phenyl-3-oxo-4-(-3-trifluoromethylphenyl)-5-methylamino-4-pyrroline

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

In this example, 4.1 g of 1-methyl-2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-4-pyrroline, was added to 100 ml of methylene chloride containing 1.0 g of sodium hydroxide, dissolved in 4.0 ml of water, and 0.28 g of benzyltriethylammonium chloride at room temperature. Dimethyl sulfate (1.17 ml) dissolved in 20 ml of methylene chloride was admixed dropwise to the aforementioned mixture at room temperature. After the addition was complete, another 0.28 g of benzyltriethylammonium was added and the mixture was stirred at room temperature for 18 hours. At the end of this time, a white precipitate was collected from the mixture by filtration. This solid was stirred with 50 ml of 1N aqueous hydrochloric acid for two hours after which it was collected with suction filtration and washed with aqueous sodium bicarbonate solution followed by water. The solid was dried affording 1.0 g of the title compound as a white powder.

Workup

  1. customat room temperature
  2. customwas admixed dropwise to the aforementioned mixture at room temperature
  3. additionAfter the addition
  4. filtrationAt the end of this time, a white precipitate was collected from the mixture by filtration
  5. stirringThis solid was stirred with 50 ml of 1N aqueous hydrochloric acid for two hours after which it
  6. filtrationwas collected with suction filtration
  7. washwashed with aqueous sodium bicarbonate solution
  8. customThe solid was dried

Sources & evidence

ORD record
ord-b4fff504db6c46ceb43b9b6088bb0deb
Source dataset
uspto-grants-1987_02
Patent number
US04643762

Reaction notes

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