Triethylamine → HCID 68456492, compound

HRID 748160Notes

Reaction equation

HRID 748160 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]([S:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][N:18]=1)[CH:13]([CH3:15])[CH3:14].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:12]([S:16][C:17]1[N:18]=[CH:19][C:20]([C:23]2[S:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:10])[N:24]=2)=[CH:21][CH:22]=1)[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 22939329HCID 22939329, compound

Product 1

HCID 68456492HCID 68456492, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl thiosalicylate (1.01 g, 6.0 mmol), 2-isobutylthio-5-cyanopyridine (1.03 g, 5.0 mmol), triethylamine (0.98 ml, 7.0 mmol) and toluene (10 ml) was refluxed under nitrogen atmosphere for 20 hrs. The reaction mixture was concentrated. The residue was subjected to a silica gel column chromatography, eluted with ethyl acetate-hexane (2:1, v/v) and recrystallized from ethyl acetate-isopropylether to give the titled compound (0.40 g, 23%).

Workup

  1. temperaturewas refluxed under nitrogen atmosphere for 20 hrs
  2. concentrationThe reaction mixture was concentrated
  3. washeluted with ethyl acetate-hexane (2:1
  4. customv/v) and recrystallized from ethyl acetate-isopropylether

Sources & evidence

ORD record
ord-c66c63cfea044ab3869726aa473aa09a
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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