Triethylamine → HCID 59750459, compound

HRID 748090Notes

Reaction equation

HRID 748090 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[CH3:12][N:13]1[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]1[C:19]#[N:20].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:12][N:13]1[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]1[C:19]1[S:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1](=[O:10])[N:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 918121,5-Dimethylpyrrole-2-carbonitrile

Product 1

HCID 59750459HCID 59750459, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (2.20 g, 13.3 mmol), 1,5-dimethyl-2-pyrrolecarbonitrile (1.40 g, 11.9 mmol), triethylamine (2.50 ml, 17.9 mmol) and toluene (7.0 ml) was refluxed for 24 hrs as described in Example 1. After cooling, the precipitated crystals were collected by filtration and recrystallized from hexane-ethanol to give the titled compound (1.30 g, 41%).

Workup

  1. temperaturewas refluxed for 24 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were collected by filtration
  4. customrecrystallized from hexane-ethanol

Sources & evidence

ORD record
ord-6c69f7d50dfb4a7093739e03ec56bd53
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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