Dimethyl Sulfate → Flurtamone

HRID 1589098Notes

Reaction equation

HRID 1589098 reaction equation
[OH-].[Na+].[C:3]1([CH:9]2[C:13](=[O:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)=[C:11]([NH2:25])[O:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.S(OC)(O[CH3:30])(=O)=O>O.C(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:3]1([CH:9]2[C:13](=[O:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:23])[F:24])[CH:16]=3)=[C:11]([NH:25][CH3:30])[O:10]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 13579285HCID 13579285, compound

Product 1

HCID 91755Flurtamone

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In this example about 1 g of solid sodium hydroxide in 4.0 ml of water was added to a mixture of 3 g of 2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran in 50 ml of methylene chloride at room temperature followed by the addition of 1.19 g of dimethyl sulfate and 0.21 g of benzyltriethyl ammonium chloride. The resulting two-phase mixture was stirred at room temperature for about two hours and then washed three times with water, dried over magnesium sulfate and then concentrated by evaporation under vacuum. The residue was then purified by chromatography over silica gel eluting with mixtures of tetrahydrofuran and chloroform affording the title compound.

Workup

  1. washwashed three times with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated by evaporation under vacuum
  4. customThe residue was then purified by chromatography over silica gel eluting with mixtures of tetrahydrofuran and chloroform affording the title compound

Sources & evidence

ORD record
ord-f7a86c49e3564ff0ae620b563589f461
Source dataset
uspto-grants-1986_02
Patent number
US04568376

Reaction notes

Loading…