Triethylamine → HCID 59750159, compound

HRID 748392Notes

Reaction equation

HRID 748392 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-485aefe5d5444cbbb49236f4c7757b32
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

Loading…