Triethylamine → HCID 23085223, compound

HRID 1442592Notes

Reaction equation

HRID 1442592 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:12](OC)(=[O:20])[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[SH:15].C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]2[S:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[C:12](=[O:20])[N:9]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 740444'-Cyanoacetophenone

Product 1

HCID 23085223HCID 23085223, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-acetylbenzonitrile (2.00 g, 14 mmol), methyl thiosalicylate (4.63 g, 28 mmol), triethylamine (2.79 g, 28 mmol) and toluene (10 ml) was heated and refluxed for 72 hours under a nitrogen flow. The reaction solution was concentrated under reduced pressure and the residue was applied to column chromatography using silica gel (100 g). Fractions eluted with hexane-ethyl acetate (3:1, v/v) were concentrated under reduced pressure. The residue was recrystallized from isopropyl ether to give the title compound (0.07 g, 2%) as crystals.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 72 hours under a nitrogen flow
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. washFractions eluted with hexane-ethyl acetate (3:1
  5. concentrationv/v) were concentrated under reduced pressure
  6. customThe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-7c2b7f6aad8e43a399b6084ba62cdaf4
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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