Dimethyl Sulfate → HCID 13579373, compound

HRID 1589083Notes

Reaction equation

HRID 1589083 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]([O:23][CH3:24])=[O: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]([O:23][CH3:24])=[O:22])[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 13579372HCID 13579372, compound

Product 1

HCID 13579373HCID 13579373, compoundYield 53.7%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In this example, 0.60 g of solid sodium hydroxide in 4.0 ml of water was added to a mixture of 4.1 g of 2-phenyl-3-oxo-4-(3-methoxycarbonylphenyl)-5-amino-2,3-dihydrofuran in 70 ml of methylene chloride at room temperature followed by the addition of 1.73 g of dimethyl sulfate and 0.30 g of benzyltriethyl ammonium chloride. The two-phase mixture was then stirred at room temperature for about 18 hours and then washed one time with water, dried over magnesium sulfate and then concentrated by evaporation under vacuum to yield an oil. The oil was triturated with 1:1 diethyl ether:methanol to afford 2.3 g of the title compound as a white powder.

Workup

  1. washwashed one time with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated by evaporation under vacuum
  4. customto yield an oil
  5. customThe oil was triturated with 1:1 diethyl ether

Sources & evidence

ORD record
ord-32d1d2bd78154752961fd399237eb1e8
Source dataset
uspto-grants-1986_02
Patent number
US04568377

Reaction notes

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