Triethylamine → HCID 59750227, compound

HRID 499513Notes

Reaction equation

HRID 499513 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-9d8e93fc69804ab7ba95a8ab56baf226
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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