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

HRID 343617

Reaction equation

HRID 343617 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-c29eec557b2e4cbaae59ed2b3d80c8de
Source dataset
uspto-grants-1999_01
Patent number
US05861517

Linked notes

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