Potassium thiocyanate → 4-methyl-N-(2,2,2-trifluoro-1-isothiocyanatoethyl)benzamide

HRID 479472Notes

Reaction equation

HRID 479472 reaction equation
Cl[CH:2]([NH:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)[C:3]([F:6])([F:5])[F:4].[S-:17][C:18]#[N:19].[K+]>CC(C)=O>[CH3:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]([NH:7][CH:2]([N:19]=[C:18]=[S:17])[C:3]([F:6])([F:5])[F:4])=[O:16])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 516872Potassium thiocyanateHCID 12150323N-(1-chloro-2,2,2-trifluoroethyl)-4-methylbenzamide

Product 1

HCID 121503244-methyl-N-(2,2,2-trifluoro-1-isothiocyanatoethyl)benzamideYield 61.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of Example 1B (2.00 g, 8.00 mmol) in acetone (35 mL) at ambient temperature was treated with potassium thiocyanate (1.60 g, 16.0 mmol). The reaction mixture was stirred for 12 hours, concentrated, and the crude residue was purified by flash chromatography (elution with 40% ethyl acetate/hexanes) to provide 1.34 g of the desired product as an off-white solid.

Workup

  1. concentrationconcentrated
  2. customthe crude residue was purified by flash chromatography (elution with 40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ae1143b2e1d6485fa6570a5ad5d8b773
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

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