Triethylamine → HCID 22939353, compound

HRID 499303Notes

Reaction equation

HRID 499303 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]#[N:27])[N:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:12]([O:19][C:20]1[N:21]=[C:22]([C:26]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:10])[N:27]=2)[CH:23]=[CH:24][CH:25]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 110529046-(Benzyloxy)picolinonitrile

Product 1

HCID 22939353HCID 22939353, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (0.40 g, 2.4 mmol), 2-benzyloxy-6-cyanopyridine (0.50 g, 2.4 mmol), triethylamine (0.50 ml, 3.6 mmol) and toluene (30 ml) was refluxed for 48 hrs as described in Example 1. The reaction mixture was concentrated under reduced pressure and recrystallized from ethanol to give the titled compound (0.21 g, 26%) as crystals.

Workup

  1. temperaturewas refluxed for 48 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3f8af14abe554bdabd5db219896090a0
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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