2-Chloroethyl isocyanate → 1-(Prop-2-yn-1-yl)imidazolidin-2-one

HRID 466753ノート

反応式

HRID 466753 の反応式
Cl[CH2:2][CH2:3][N:4]=[C:5]=[O:6].[CH2:7]([NH2:10])[C:8]#[CH:9]>C1COCC1>[CH2:7]([N:10]1[CH2:2][CH2:3][NH:4][C:5]1=[O:6])[C:8]#[CH:9]

参加物

4

反応物 2

HCID 160352-Chloroethyl isocyanateHCID 239041Propargylamine

生成物 1

HCID 156696571-(Prop-2-yn-1-yl)imidazolidin-2-one収率 81.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Chloroethyl isocyanate (12.2 g, 0.11 mol) was added at 0° C. to a stirred solution of propargylamine (6.6 g, 0.12 mol) in THF (200 mL). The solution was allowed to warm to room temperature and sodium hydride (5.5 g of 50% in oil, washed with ether to remove the oil) was added. The reaction was quenched with acetic acid (6.0 mL), the THF was removed under reduced pressure, and the residue was partitioned between ethyl acetate and water. The ethyl acetate was evaporated and the residual solid was crystallized from ethyl acetate; Skellysolve B to give 11.1 g of 1-(2-propynyl)-2-imidazolidinone, m.p. 110°-115° C.

後処理

  1. washsodium hydride (5.5 g of 50% in oil, washed with ether
  2. customto remove the oil)
  3. additionwas added
  4. customThe reaction was quenched with acetic acid (6.0 mL)
  5. customthe THF was removed under reduced pressure
  6. customthe residue was partitioned between ethyl acetate and water
  7. customThe ethyl acetate was evaporated
  8. customthe residual solid was crystallized from ethyl acetate

出典と根拠

ORDレコード
ord-a9ff737be36947399e09167a27356b8b
出典データセット
uspto-grants-1992_10
特許番号
US05157124

反応ノート

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