Triethylamine → HCID 22939582, compound

HRID 499587Notes

Reaction equation

HRID 499587 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-c7990f68089b4d00afc500d1990b032c
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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