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

HRID 2226162ノート

反応式

HRID 2226162 の反応式
[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]

参加物

4

反応物 2

HCID 944603,5-Dichlorophenyl isocyanateHCID 14326200HCID 14326200、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-12059fc4cbf04792b4d452cf1c098e29
出典データセット
uspto-grants-1994_09
特許番号
US05346913

反応ノート

読み込み中…