Triethylamine → HCID 59750227, compound

HRID 748331Notes

Reaction equation

HRID 748331 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH2:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[CH:6]=[CH:5][CH:4]=1)#[N:2].[C:18](OC)(=[O:26])[C:19]1[C:20](=[CH:22][CH:23]=[CH:24][CH:25]=1)[SH:21].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:26]=[C:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[S:21][C:1]([C:3]2[N:8]=[C:7]([CH2:9][P:10](=[O:17])([O:11][CH2:12][CH3:13])[O:14][CH2:15][CH3:16])[CH:6]=[CH:5][CH:4]=2)=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 86596469HCID 86596469, compound

Product 1

HCID 59750227HCID 59750227, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diethyl (6-cyano-2-pyridyl)methylphosphonate (1.4 g, 5.8 mmol) and methyl thiosalicylate (1.9 g, 11.6 mmol) were dissolved in toluene (8 ml), and triethylamine (4.0 ml, 28.6 mmol) was added thereto. The mixture was refluxed for 13 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with ethyl acetate-methanol (10:1, v/v) were collected, concentrated and recrystallized from diisopropyl ether-ethanol to give the titled compound (510 mg, 22%) as pale yellow crystals.

Workup

  1. temperatureThe mixture was refluxed for 13 hrs
  2. customThe solvent was evaporated
  3. washThe fractions eluted with ethyl acetate-methanol (10:1
  4. customv/v) were collected
  5. concentrationconcentrated
  6. customrecrystallized from diisopropyl ether-ethanol

Sources & evidence

ORD record
ord-1125d8e1dccb479aa18fc4b863c64891
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

Loading…