Triethylamine → 1-Allyl-3-(5-chloro-2-methylphenyl)-2-thioxo-imidazolidin-4-one

HRID 399607

反応式

HRID 399607 の反応式
[CH2:1]([NH:4][CH2:5][C:6]([OH:8])=O)[CH:2]=[CH2:3].[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:19])=[C:14]([N:16]=[C:17]=[S:18])[CH:15]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([N:4]1[CH2:5][C:6](=[O:8])[N:16]([C:14]2[CH:15]=[C:10]([Cl:9])[CH:11]=[CH:12][C:13]=2[CH3:19])[C:17]1=[S:18])[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 295195-Chloro-2-methylphenyl isothiocyanateHCID 76651N-Allylglycine

生成物 1

HCID 189682071-Allyl-3-(5-chloro-2-methylphenyl)-2-thioxo-imidazolidin-4-one収率 15.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of N-allyl glycine (17.4 g), 5-chloro-2-methylphenyl-isothiocyanate (20.1 g), triethylamine (20.2 g), and methylene chloride (150 mL) was heated at reflux for 2 hours. The reaction mixture was evaporated to dryness. Purification was achieved by flash chromatography on silica gel (methylene chloride). Recrystallization from Hexane-EtOAc afford the title compound (4.8 g) as yellow solid, m.p. 106°-109° C. Anal. Calcd. for. C13H13N2O Cl S: C, 55.61; H, 4.67; N, 9.98. Found: C, 55.45; H, 4.56; N, 9.72. Mass spectrum (EI, M.+) m/z 280.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe reaction mixture was evaporated to dryness
  4. customPurification
  5. customRecrystallization from Hexane-EtOAc

出典と根拠

ORDレコード
ord-fd133eec96734c52b5851dd185d36571
出典データセット
uspto-grants-1998_10
特許番号
US05821372

関連ノート

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