Triethylamine → 1-Allyl-3-(2,6-dimethylphenyl)-2-thioxo-imidazolidin-4-one

HRID 343617

反応式

HRID 343617 の反応式
[CH2:1]([NH:4][CH2:5][C:6]([OH:8])=O)[CH:2]=[CH2:3].[CH3:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1[N:17]=[C:18]=[S:19].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([N:4]1[CH2:5][C:6](=[O:8])[N:17]([C:11]2[C:12]([CH3:16])=[CH:13][CH:14]=[CH:15][C:10]=2[CH3:9])[C:18]1=[S:19])[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 76651N-AllylglycineHCID 879762,6-Xylyl isothiocyanate

生成物 1

HCID 114143011-Allyl-3-(2,6-dimethylphenyl)-2-thioxo-imidazolidin-4-one収率 16.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of N-allyl glycine (17.4 g), 2,6-dimethylphenyl-isothiocyanate (20 g), triethylamine (20.2 g), and methylene chloride (150 mL) was heated at reflux for 3 hours. The reaction mixture was evaporated to dryness. The residual gum was dissolved in diethyl ether, then treated with etheral hydrogen chloride. A white solid formed. The solid was filtered and discarded. The filtrate was concentrated to a residue. The residue was chromatographed on silica gel (CH2Cl2) to give title compound (5.2 g) as an orange solid, m.p. 43°-46° C. Anal. Calcd. for. C14H16N2OS: C, 64.59; H, 6.19; N, 10.76. Found: C, 64.52; H, 6.08; N, 10.66. Mass spectrum (EI, M.+) m/z 260.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customThe reaction mixture was evaporated to dryness
  4. dissolutionThe residual gum was dissolved in diethyl ether
  5. additiontreated with etheral hydrogen chloride
  6. customA white solid formed
  7. filtrationThe solid was filtered
  8. concentrationThe filtrate was concentrated to a residue
  9. customThe residue was chromatographed on silica gel (CH2Cl2)

出典と根拠

ORDレコード
ord-c29eec557b2e4cbaae59ed2b3d80c8de
出典データセット
uspto-grants-1999_01
特許番号
US05861517

関連ノート

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