2-Methylbenzenesulfonic acid → Dithiophenylacetic Acid, 2-(2-pyridinyl)ethyl Ester

HRID 749513

Reaction equation

HRID 749513 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[C:7]([OH:9])=[O:8].[CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)=[CH2:16].C1(C)C(S(O)(=O)=O)=CC=CC=1>C1C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[C:7]([O:9][CH2:16][CH2:15][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)=[O:8]

Participants

5

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 75212-VinylpyridineHCID 20443Di(2-thienyl)acetic acid

Product 1

HCID 86589915Dithiophenylacetic Acid, 2-(2-pyridinyl)ethyl Ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The crude product of newly synthesized dithiophenyl acetic acid (10 g, 59 mmol theoretically), freshly distilled 2-vinylpyridine (6.25 g, 59 mmol), and 1 mol % toluene sulfonic acid were dissolved in benzene and placed in a round bottom flask equipped with a vigreaux column and magnetic stirbar. The reaction was then heated to reflux and allowed to react for 16 hours. The viscous liquid that remained after the solvent was removed was then purified by column chromatography (silica 2/1 v/v hexane/ethyl acetate). Yield=3.9 g. 1 H NMR (CDCl3) δ=3.042 (t, 2 H), δ=3.573 (t, 2 H), δ=4.233 (s, 2 H) δ=6.968-7.476 (m, 8 H), δ=8.467, (d, 1 H). 13C NMR (CDCl3) δ=35.627 (CH2), δ=36.180 (CH2), δ=58.323 (CH2), δ=121.932 (CH), δ=123.383 (CH2), δ=127.501 (CH), δ=128.818 (CH), δ=129.346 (CH), δ=137.272 (C), δ=149.668 (CH), δ=159.305 (C), δ=235.369 (C═S).

Workup

  1. customplaced in a round bottom flask
  2. customequipped with a vigreaux column and magnetic stirbar
  3. temperatureThe reaction was then heated
  4. temperatureto reflux
  5. customto react for 16 hours
  6. customwas removed
  7. customwas then purified by column chromatography (silica 2/1 v/v hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3f9df8f224f845128c7ad2679ab28b3f
Source dataset
uspto-grants-2008_07
Patent number
US07402690B2

Linked notes

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