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

HRID 742280

Reaction equation

HRID 742280 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. 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.

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-b07bece6fde44ec48ba20a8d73c1932d
Source dataset
uspto-grants-1996_09
Patent number
US05554607

Linked notes

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