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

HRID 343617

반응식

HRID 343617 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c29eec557b2e4cbaae59ed2b3d80c8de
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05861517

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