Triethylamine → HCID 68459271, compound

HRID 748116Notes

Reaction equation

HRID 748116 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].C(O[C:16]1[CH:17]=[CH:18][C:19]([C:22]#N)=[N:20][CH:21]=1)(=O)C.[C:24]([O:27]C1C(C#N)=NC=CC=1)(=[O:26])[CH3:25].[CH2:36]([N:38](CC)CC)C>C1(C)C=CC=CC=1>[C:24]([O:27][CH2:22][C:19]1[CH:18]=[CH:17][C:16]([C:36]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:10])[N:38]=2)=[CH:21][N:20]=1)(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939311HCID 22939311, compoundHCID 229393796-Cyanopyridin-3-yl acetate

Product 1

HCID 68459271HCID 68459271, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (0.58 g, 3.43 mmol), a mixture of 5-acetoxy-2-cyanopyridine and 3-acetoxy-2-cyanopyridine (0.60 g, 3.43 mmol), triethylamine (0.72 ml, 5.15 mmol) and toluene (100 ml) was refluxed for 48 hrs as described in Example 1. The solvent was concentrated under reduced pressure. The residue was recrystallized from ethanol to give the titled compound (0.30 g, 29%) as crystals.

Workup

  1. temperaturewas refluxed for 48 hrs
  2. concentrationThe solvent was concentrated under reduced pressure
  3. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-eb747d87bc62457cb5fc264f7bc4f302
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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