Diethyl Ether → HCID 18770730, compound

HRID 479500Notes

Reaction equation

HRID 479500 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9](Cl)[C:10]([Cl:13])([Cl:12])[Cl:11])=[O:7])=[CH:4][CH:3]=1.[S-:17][C:18]#[N:19].[K+].C(OCC)C>CC(C)=O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]([N:19]=[C:18]=[S:17])[C:10]([Cl:13])([Cl:12])[Cl:11])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 516872Potassium thiocyanateHCID 123415754-Chloro-N-(1,2,2,2-tetrachloroethyl)benzamide

Product 1

HCID 18770730HCID 18770730, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of Example 41B (1.91 g, 6.31 mmol) in acetone (30 mL) at ambient temperature was treated with potassium thiocyanate (1.38 g, 14.1 mmol). The mixture was stirred for 6 hours and solids were removed by filtration. The filtrate was concentrated to provide a yellow residue. The residue was treated with diethyl ether, and the suspension was sonicated and filtered. Concentration of the residue and purification by recrystallization (25% ethyl acetate/hexanes) provided 1.85 mg of the desired product as a yellow solid.

Workup

  1. customsolids were removed by filtration
  2. concentrationThe filtrate was concentrated
  3. customto provide a yellow residue
  4. customthe suspension was sonicated
  5. filtrationfiltered
  6. customConcentration of the residue and purification
  7. customby recrystallization (25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-42d21bb13fdc480e9595ba40a3b0d2b5
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

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