Dimethyl Sulfate → HCID 13672731, compound

HRID 364825Notes

Reaction equation

HRID 364825 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)=[C:9]([NH2:23])[O:8]2)[CH:2]=1.[OH-].[Na+].[CH3:26]OS(OC)(=O)=O>C(Cl)Cl.O.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=3)=[C:9]([NH:23][CH3:26])[O:8]2)[CH:2]=1

Participants

7

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium Hydroxide2×HCID 13672730HCID 13672730, compound

Product 1

HCID 13672731HCID 13672731, compound

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Two (2) grams of 2-(pyrid-3-yl)-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran was dissolved in 50 ml of methylene chloride at room temperature. 0.24 g of sodium hydroxide, dissolved in the minimum amount of water needed to dissolve the sodium hydroxide, and 0.46 g of benzyltrimethylammonium chloride was added. Then a solution containing 0.79 g of dimethylsulfate in about 10 ml of methylene chloride was slowly added and the mixture stirred for two days at room temperature. The mixture was then washed with water, dried over magnesium sulfate and evaporatyed to a solid residue. The residue was triturated with 30% vol. ethyl acetate: 70% petroleum ether and filtered.

Workup

  1. additionwas added
  2. additionwas slowly added
  3. washThe mixture was then washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe residue was triturated with 30% vol. ethyl acetate
  6. filtration70% petroleum ether and filtered

Sources & evidence

ORD record
ord-b46d1f5f27f642f59f1607f4c08157c1
Source dataset
uspto-grants-1986_08
Patent number
US04606756

Reaction notes

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