Triethylamine → HCID 59750302, compound

HRID 499373Notes

Reaction equation

HRID 499373 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:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([S:20][CH:21]([CH3:23])[CH3:22])[N:15]=1)#[N:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH:21]([S:20][C:16]1[N:15]=[C:14]([C:12]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:10])[N:13]=2)[CH:19]=[CH:18][CH:17]=1)([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939361HCID 22939361, compound

Product 1

HCID 59750302HCID 59750302, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (1.21 g, 7.2 mmol), 2-cyano-6-isopropylthiopyridine (1.40 g, 7.9 mmol), triethylamine (1.5 ml, 10.8 mmol) and toluene (30 ml) was refluxed for 48 hrs. The reaction mixture was concentrated under reduced pressure to give the precipitated crystals, which were recrystallized from ethyl acetate-hexane to give the titled compound (0.24 g, 10%).

Workup

  1. temperaturewas refluxed for 48 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give the precipitated crystals, which
  4. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-537a8887b9cf434894527682db3e06d6
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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