Triethylamine → HCID 58610092, compound

HRID 1442595Notes

Reaction equation

HRID 1442595 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[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>[O:21]=[C:13]1[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[S:16][C:1]([C:3]2[CH:4]=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=2)=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 737204N-(3-cyanophenyl)acetamide

Product 1

HCID 58610092HCID 58610092, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-(3-cyanophenyl)acetamide (2.00 g, 13 mmol), methyl thiosalicylate (3.20 g, 19 mmol), triethylamine (2.30 g, 23 mmol) and toluene (15 ml) was heated and refluxed for 25 hours under a nitrogen flow. The solvent was concentrated under reduced pressure. After washing with isopropyl ether and ethanol, the residue was recrystallized from tetrahydrofuran-ethyl acetate to give the title compound (0.07 g, 2%) as crystals.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 25 hours under a nitrogen flow
  3. concentrationThe solvent was concentrated under reduced pressure
  4. washAfter washing with isopropyl ether and ethanol
  5. customthe residue was recrystallized from tetrahydrofuran-ethyl acetate

Sources & evidence

ORD record
ord-e07be8d114404958bee7643d81a88cd6
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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