Hydrochloric Acid → HCID 21966412, compound

HRID 2057118Notes

Reaction equation

HRID 2057118 reaction equation
[OH-].[Na+].[OH:3][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[S:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.[Na].Br[CH2:21][C:22]([O:24]CC)=[O:23].Cl>O1CCCC1.O>[C:22]([CH2:21][O:3][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[S:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([OH:24])=[O:23]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 57438571-Hydroxy-9H-thioxanthen-9-one2×

Product 1

HCID 21966412HCID 21966412, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

24 g sodium hydroxide was refluxed in 400 ml tetrahydrofuran for five minutes. 22.8 g (0.1 mols) hydroxythioxanthone was added and reflux continued for 1 hour, during which time the colour changed to bright red, indicating the formation of the sodium salt of hydroxythioxanthone. 35.1 g (0.21 mols) of ethyl bromoacetate was added and reflux was continued for three hours. After cooling to room temperature, 400 ml of deionised water were added with stirring, and the tetrahydrofuran was distilled out to yield a clear red solution. Reflux was continued for a further 2 hours in order to hydrolyse all the ester intermediate. The solution was then cooled to 50 C and 400 ml 1.0 M aqueous hydrochloric acid was added with stirring, causing the solid product to precipitate out. After refluxing for five minutes to be sure that all the sodium salt was converted to free acid, the solution was cooled to room temperature and stirred for two hours before filtering off the solid, washing with 400 ml deionised water and drying in a vacuum oven at 80 C.

Workup

  1. temperaturereflux
  2. temperaturereflux
  3. waitwas continued for three hours
  4. distillationthe tetrahydrofuran was distilled out
  5. customto yield a clear red solution
  6. temperatureReflux
  7. waitwas continued for a further 2 hours in order
  8. additionwas added
  9. stirringwith stirring
  10. customto precipitate out
  11. temperatureAfter refluxing for five minutes
  12. temperaturethe solution was cooled to room temperature
  13. stirringstirred for two hours
  14. filtrationbefore filtering off the solid
  15. washwashing with 400 ml
  16. customdrying in a vacuum oven at 80 C

Sources & evidence

ORD record
ord-97b7e0e1ae6a4a1ea302abd7d052a00d
Source dataset
uspto-grants-2008_02
Patent number
US07335782B2

Reaction notes

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