Water → 2,6-Dithia-s-indacene-4,8-dione

HRID 638515Notes

Reaction equation

HRID 638515 reaction equation
C(SC[C:11]1[C:12](=[O:48])[C:13]([CH2:38][S:39][C:40](=O)C2C=CC=CC=2)=[C:14](CSC(=O)C2C=CC=CC=2)[C:15](=[O:27])[C:16]=1[CH2:17][S:18][C:19](=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[OH-].[Na+].O>C(O)CO>[CH:38]1[S:39][CH:40]=[C:14]2[C:15](=[O:27])[C:16]3[C:11]([C:12](=[O:48])[C:13]=12)=[CH:19][S:18][CH:17]=3

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13587485HCID 13587485, compound

Product 1

HCID 2884982,6-Dithia-s-indacene-4,8-dioneYield 73%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

48.5 g (68.5 millimoles) of 2,3,5,6-tetra-(benzoylthiomethyl)-p-benzoquinone were suspended in 450 ml of ethylene glycol, and 32.8 g (411 millimoles) of 50% strength sodium hydroxide solution were added, while stirring thoroughly. A strong jet of compressed air was then passed through the reaction mixture, and the latter was slowly heated up. At an internal temperature of 70° C., the dark mixture became homogeneous. The internal temperature was increased to 90°-100° C., and thorough stirring was continued at this temperature for 5 hours, while compressed air was continuously passed through. The mixture was cooled, 700 ml of water were added and stirring was continued for a further 0.5 hour, while cooling with ice. The solid material was filtered off under suction and washed with a large amount of water. 11.0 g (73%) of 4,8-dihydrobenzo[1,2-c:4,5-c']dithiophene-4,8-dione of melting point 340° C. were isolated.

Workup

  1. temperaturethe latter was slowly heated up
  2. customAt an internal temperature of 70° C.
  3. temperatureThe internal temperature was increased to 90°-100° C.
  4. stirringthorough stirring
  5. temperatureThe mixture was cooled
  6. stirringstirring
  7. waitwas continued for a further 0.5 hour
  8. temperaturewhile cooling with ice
  9. filtrationThe solid material was filtered off under suction
  10. washwashed with a large amount of water

Sources & evidence

ORD record
ord-57db12f60eb145f0b6f4440d1f2f477d
Source dataset
uspto-grants-1985_12
Patent number
US04562004

Reaction notes

Loading…