Quinone → 2-Thioxonaphth[2,3-d] [1,3]dithiol-5,8-dione

HRID 41605

反応式

HRID 41605 の反応式
Br[CH2:2][C:3]1[S:4][C:5](=[S:10])[S:6][C:7]=1[CH2:8]Br.[C:11]1(=[O:18])[CH:16]=[CH:15][C:14](=[O:17])[CH:13]=[CH:12]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>[I-].C([N+](CC)(CC)CC)C.C(#N)C>[S:10]=[C:5]1[S:4][C:3]2[CH:2]=[C:12]3[C:13](=[CH:8][C:7]=2[S:6]1)[C:14](=[O:17])[CH:15]=[CH:16][C:11]3=[O:18]

参加物

6

反応物 3

HCID 4650QuinoneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 110884794,5-Bis(bromomethyl)-1,3-dithiol-2-thione

生成物 1

HCID 154688092-Thioxonaphth[2,3-d] [1,3]dithiol-5,8-dione収率 78%

試薬・触媒・溶媒 2

HCID 6225Tetraethylammonium Iodide触媒HCID 6342Acetonitrile溶媒

実験手順

In a vessel, the 4,5-bis(bromomethyl)-1,3-dithiol-2-thione: 1-3 (1.10 g), tetraethylammonium iodide (0.38 g), p-benzoquinone (2.77 g), and acetonitrile (60 mL) were charged, and then refluxed for 1 hour. Thereafter, dichloro dicyano benzoquinone (1.62 g) was added in the resultant mixture, and then refluxed for 7 hours. After completion of the reflux, the solvent was distilled away, and methanol was added in the vessel, and then the precipitate was recovered through filtration. The precipitate was washed with methanol, distilled water, and ether in this order, the obtained residue was dissolved in chloroform, and then filtered. The obtained filtrate was recrystallized, to thereby obtain 2-thioxonaphth[2,3-d] [1,3]dithiol-5,8-dione: 1-4 in a yield of 78%. The target compound was identified through NMR analysis: 1H-NMR (CDCl3, TMS) σ: 7.04 (s, 2H), 8.15 (s, 2H).

後処理

  1. temperaturerefluxed for 1 hour
  2. temperaturerefluxed for 7 hours
  3. distillationAfter completion of the reflux, the solvent was distilled away
  4. additionmethanol was added in the vessel
  5. filtrationthe precipitate was recovered through filtration
  6. washThe precipitate was washed with methanol
  7. distillationdistilled water, and ether in this order
  8. dissolutionthe obtained residue was dissolved in chloroform
  9. filtrationfiltered
  10. customThe obtained filtrate was recrystallized

出典と根拠

ORDレコード
ord-52e73abbae0745c5ae679ecdd815abf1
出典データセット
uspto-grants-2013_09
特許番号
US08530673B2

関連ノート

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