Triethylamine → HCID 59750122, compound

HRID 499638Notes

Reaction equation

HRID 499638 reaction equation
[CH3:1][C:2]([CH3:21])([CH2:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]#[N:20])[CH:14]=1)[C:3]([O:5][CH2:6][CH2:7][Si:8]([CH3:11])([CH3:10])[CH3:9])=[O:4].[C:22](OC)(=[O:30])[C:23]1[C:24](=[CH:26][CH:27]=[CH:28][CH:29]=1)[SH:25].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][C:2]([CH3:21])([CH2:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]2[S:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[C:22](=[O:30])[N:20]=2)[CH:14]=1)[C:3]([O:5][CH2:6][CH2:7][Si:8]([CH3:10])([CH3:9])[CH3:11])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939565HCID 22939565, compound

Product 1

HCID 59750122HCID 59750122, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(Trimethylsilyl)ethyl 2,2-dimethyl-3-(2-cyano-4-pyridyl)propionate (0.68 g, 2.2 mmol) and methyl thiosalicylate (0.60 g, 3.6 mmol) were dissolved in toluene (2.5 ml), and triethylamine (0.56 ml, 4.0 mmol) was added thereto. The reaction mixture was refluxed for 16 hrs and subjected to a silica gel (30 g) column chromatography. The fractions eluted with hexane-ethyl acetate (5:1, v/v) were collected and concentrated to give the titled compound (0.52 g, 53%) as white crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hrs
  2. washThe fractions eluted with hexane-ethyl acetate (5:1
  3. customv/v) were collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-230a459f154e497b948d83a0396214dd
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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