Diethyl Sulfate → HCID 15615996, compound

HRID 476524Notes

Reaction equation

HRID 476524 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH2:6][S:7]([NH:10][CH2:11][C:12]([NH2:14])=O)(=[O:9])=[O:8].[OH-].[Na+].[CH2:22](OS(OCC)(=O)=O)[CH3:23]>ClCCl.O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH2:22]([N:10]([CH2:11][C:12]#[N:14])[S:7]([CH2:6][C:5]1[CH:15]=[CH:16][CH:17]=[C:3]([C:2]([F:19])([F:18])[F:1])[CH:4]=1)(=[O:9])=[O:8])[CH3:23]

Participants

7

Reactant 3

HCID 6163Diethyl SulfateHCID 14798Sodium HydroxideHCID 14517965HCID 14517965, compound

Product 1

HCID 15615996HCID 15615996, compound

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

In this example 2 g of 3-trifluoromethylbenzylsulfonamidoacetamide was dissolved in 30 ml of dichloromethane. To this was added 0.32 g of sodium hydroxide dissolved in a minimum amount of water and 0.46 of benzyltriethylammonium chloride. A solution of 1.1 ml of diethylsulfate in 5 ml of dichloromethane was added dropwise. The reaction mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and the dichloromethane layer was separated. The water phase is extracted with dichloromethane. The organic phases are combined, dried over magnesium sulfate, filtered and stripped. Trituration of the resulting solid residue yielded 1.4 g of title compound as a white solid; m.p. 67° to 68.5° C.

Workup

  1. customthe dichloromethane layer was separated
  2. extractionThe water phase is extracted with dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-4c49a9d70990429fa7a0674c15e7f948
Source dataset
uspto-grants-1989_12
Patent number
US04885027

Reaction notes

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