Triethylamine → HCID 59750159, compound

HRID 499574Notes

Reaction equation

HRID 499574 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[N:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][CH:6]=1.[C:13](OC)(=[O:21])[C:14]1[C:15](=[CH:17][CH:18]=[CH:19][CH:20]=1)[SH:16].C(N(CC)CC)C>C1(C)C=CC=CC=1>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[N:10]=[C:9]([C:11]2[S:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[C:13](=[O:21])[N:12]=2)[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939443HCID 22939443, compound

Product 1

HCID 59750159HCID 59750159, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-(3-Hydroxypropyl)-2-pyridinecarbonitrile (2.2 g, 13.6 mmol) and methyl thiosalicylate (3.7 g, 22.0 mmol) were dissolved in toluene (15 ml), and triethylamine (3.0 ml, 21.7 mmol) was added thereto. The reaction mixture was refluxed for 30 hrs and subjected to a silica gel (170 g) column chromatography. The fractions eluted with ethyl acetate were collected and concentrated to give the titled compound (0.61 g, 15%) as white crystals.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 hrs
  2. washThe fractions eluted with ethyl acetate
  3. customwere collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bdd2aa9173da4e34926f44c3c43475d3
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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