Triethylamine → HCID 22939582, compound

HRID 748405Notes

Reaction equation

HRID 748405 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[O:16])[CH:6]=[CH:5][CH:4]=1)#[N:2].[C:24](OC)(=[O:32])[C:25]1[C:26](=[CH:28][CH:29]=[CH:30][CH:31]=1)[SH:27].C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:32]=[C:24]1[C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[S:27][C:1]([C:3]2[N:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH2:19][Si:20]([CH3:22])([CH3:23])[CH3:21])=[O:16])[CH:6]=[CH:5][CH:4]=2)=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939471HCID 22939471, compound

Product 1

HCID 22939582HCID 22939582, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(Trimethylsilyl)ethyl 7-(6-cyano-2-pyridyl)heptanoate (0.52 g, 1.6 mmol) and methyl thiosalicylate (0.43 g, 2.5 mmol) were dissolved in toluene (2 ml), and triethylamine (0.44 ml, 2.3 mmol) was added thereto. The reaction mixture was refluxed for 16 hrs and subjected to a silica gel (35 g) column chromatography. The fractions eluted with hexane-ethyl acetate (4:1, v/v) were collected and concentrated to give the titled compound (0.38 g, 27%) as a yellow oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hrs
  2. washThe fractions eluted with hexane-ethyl acetate (4:1
  3. customv/v) were collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-38ad572b8b87424ca33f4f7da667e8d1
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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