3,5-Dichlorophenyl isocyanate → 3-(3,5-Dichlorophenyl)-5-methyl-1-(prop-2-yn-1-yl)imidazolidine-2,4-dione

HRID 2226162Notes

Reaction equation

HRID 2226162 reaction equation
[CH2:1]([NH:4][CH:5]([CH3:10])[C:6]([O:8]C)=O)[C:2]#[CH:3].[Cl:11][C:12]1[CH:13]=[C:14]([N:19]=[C:20]=[O:21])[CH:15]=[C:16]([Cl:18])[CH:17]=1>C1(C)C=CC=CC=1>[CH2:1]([N:4]1[CH:5]([CH3:10])[C:6](=[O:8])[N:19]([C:14]2[CH:15]=[C:16]([Cl:18])[CH:17]=[C:12]([Cl:11])[CH:13]=2)[C:20]1=[O:21])[C:2]#[CH:3]

Participants

4

Reactant 2

HCID 944603,5-Dichlorophenyl isocyanateHCID 14326200HCID 14326200, compound

Product 1

HCID 143262013-(3,5-Dichlorophenyl)-5-methyl-1-(prop-2-yn-1-yl)imidazolidine-2,4-dioneYield 86.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 2-propargylaminopropionate (10 g, 0.07 mole) in toluene (100 mL) with 2 drops of stannous octonoate was added 3,5-dichlorophenylisocyanate (14.5 g, 0,077 mole) in small portions. The resulting mixture was heated at 100° C. for 3 hours. It was then washed with water twice and dried over sodium sulfate. Solvent was evaporated to give a thick, yellow oil. Material was further purified by passing it through a silica gel column using 30/70 ethyl acetate/hexane as eluent to give 18 grams of a light yellow oil which solidified on standing. The solids were triturated in boiling hexane and collected by suction filtration; mp 105°-106° C., NMR and elemental analysis confirmed the desired structure.

Workup

  1. washIt was then washed with water twice
  2. dry with materialdried over sodium sulfate
  3. customSolvent was evaporated
  4. customto give a thick, yellow oil
  5. customMaterial was further purified

Sources & evidence

ORD record
ord-12059fc4cbf04792b4d452cf1c098e29
Source dataset
uspto-grants-1994_09
Patent number
US05346913

Reaction notes

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