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

HRID 742280

反応式

HRID 742280 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. C14H16N2O S: C, 64.59; H, 6.19; N, 10.76. Found: (2, 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-b07bece6fde44ec48ba20a8d73c1932d
出典データセット
uspto-grants-1996_09
特許番号
US05554607

関連ノート

読み込み中…