Triethylamine → HCID 22939487, compound

HRID 748397Notes

Reaction equation

HRID 748397 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])=[O:14])[CH:6]=[CH:5][CH:4]=1)#[N:2].[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>[O:30]=[C:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[S:25][C:1]([C:3]2[N:8]=[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:19])[CH3:21])=[O:14])[CH:6]=[CH:5][CH:4]=2)=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939448HCID 22939448, compound

Product 1

HCID 22939487HCID 22939487, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(Trimethylsilyl)ethyl 5-(6-cyano-2-pyridyl)valerate (1.0 g, 3.3 mmol) and methyl thiosalicylate (0.85 g, 5.0 mmol) were dissolved in toluene (4 ml), and triethylamine (0.85 ml, 8.4 mmol) was added thereto. The reaction mixture was refluxed for 10 hrs and subjected to a silica gel (75 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 white crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 10 hrs
  2. washThe fractions eluted with hexane-ethyl acetate (4:1
  3. customv/v) were collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-092ae836bc734f40a034770d1f457c89
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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