Triethylamine → HCID 22939276, compound

HRID 499642Notes

Reaction equation

HRID 499642 reaction equation
[C:1]([C:3]1[C:8]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:7][CH:6]=[C:5]([C:18]#[N:19])[N:4]=1)#[N:2].[C:20](OC)(=[O:28])[C:21]1[C:22](=[CH:24][CH:25]=[CH:26][CH:27]=1)[SH:23].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:1]([C:3]1[C:8]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])=[CH:7][CH:6]=[C:5]([C:18]2[S:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[C:20](=[O:28])[N:19]=2)[N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939312HCID 22939312, compound

Product 1

HCID 22939276HCID 22939276, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl 3-(2,6-dicyano-3-pyridyl)propanoate (0.31 g, 1.20 mmol) and methyl thiosalicylate (0.40 g, 2.40 mmol) were dissolved in toluene (30 ml), and triethylamine (0.75 ml, 5.41 mmol) was added thereto. The mixture was refluxed for 18 hrs, and the solvent was evaporated. The residue was washed with hexane-ethyl acetate to give the titled compound (0.12 g, 25%) as white amorphous solid.

Workup

  1. temperatureThe mixture was refluxed for 18 hrs
  2. customthe solvent was evaporated
  3. washThe residue was washed with hexane-ethyl acetate

Sources & evidence

ORD record
ord-aaf38e3795324f968fdf8d685161c96f
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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