Triethylamine → HCID 59750232, compound

HRID 748446Notes

Reaction equation

HRID 748446 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-66c69459dde746f2a4c90ee7434b5037
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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