Potassium cyanate → 4-methyl-N-(2,2,2-trichloro-1-isocyanatoethyl)benzamide

HRID 479496Notes

Reaction equation

HRID 479496 reaction equation
[CH3:1][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.[O-:17][C:18]#[N:19].[K+]>CC(C)=O>[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]([N:19]=[C:18]=[O:17])[C:10]([Cl:13])([Cl:12])[Cl:11])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11378442Potassium cyanateHCID 123415764-Methyl-N-(1,2,2,2-tetrachloroethyl)benzamide

Product 1

HCID 187707404-methyl-N-(2,2,2-trichloro-1-isocyanatoethyl)benzamideYield 60.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of Example 37D (1.00 g, 3.32.00 mmol) in acetone (20 mL) at ambient temperature was treated with potassium cyanate (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 50% ethyl acetate/hexanes) to provide 620 mg of the desired product as an off-white solid.

Workup

  1. concentrationconcentrated
  2. customthe crude residue was purified by flash chromatography (elution with 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-67496c04989840a9921184ec86f9958e
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

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