Triethylamine → HCID 59750232, compound

HRID 499628Notes

Reaction equation

HRID 499628 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]#[N:15])[CH:9]=2)[C:4]1=[O:16])[CH3:2].[C:17](OC)(=[O:25])[C:18]1[C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)[SH:20].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:1]([N:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[S:20][C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[C:17](=[O:25])[N:15]=3)[CH:9]=2)[C:4]1=[O:16])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939362HCID 22939362, compound

Product 1

HCID 59750232HCID 59750232, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(3-Ethyl-2-oxo-1-imidazolidinyl)-2-pyridinecarbonitrile (0.16 g, 0.76 mmol) and methyl thiosalicylate (0.42 g, 2.5 mmol) was dissolved in toluene (4 ml), and triethylamine (2.0 ml, 14.3 mmol) was added thereto. The mixture was refluxed for 9 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate were collected, concentrated and recrystallized from tetrahydrofuran-hexane to give the titled compound (0.14 g, 51%) as white crystals.

Workup

  1. temperatureThe mixture was refluxed for 9 hrs
  2. customThe solvent was evaporated
  3. washThe fractions eluted with ethyl acetate
  4. customwere collected
  5. concentrationconcentrated
  6. customrecrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-4e75ca71b1b6446ca299a8fdc7abb353
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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