Iodine → HCID 22118366, compound

HRID 1275447Notes

Reaction equation

HRID 1275447 reaction equation
[C:1]([C:4]1[C:5]([CH3:18])=[C:6]2[C:11](=[C:12]([CH3:14])[CH:13]=1)[S:10][CH2:9][C:8]([CH3:16])([CH3:15])[C:7]2=[O:17])(=[O:3])C.II.[OH-:21].[K+].[OH-].[Na+]>O.C(O)CO.N1C=CC=CC=1>[C:1]([C:4]1[C:5]([CH3:18])=[C:6]2[C:11](=[C:12]([CH3:14])[CH:13]=1)[S:10][CH2:9][C:8]([CH3:16])([CH3:15])[C:7]2=[O:17])([OH:3])=[O:21]

Participants

8

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 22118438HCID 22118438, compound

Product 1

HCID 22118366HCID 22118366, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 962WaterSolventHCID 1049PyridineSolvent2×

Procedure

A mixture containing 10.8 g (41 mmol) of 6-acetyl-3,3,5,8-tetramethylthiochroman-4-one, 12.6 g (50 mmol) of iodine and 9.8 g (124 mmol) of pyridine was heated at 110~110° C. for 6 hours. After the completion of the reaction, excess pyridine was distilled off under reduced pressure, and to the residue were added 50 ml of ethylene glycol, 20 ml of water and 11 g (167 mmol) of potassium hydroxide. The mixture was refluxed under heat for 2 hours. After the reaction mixture was allowed to cool, 200 ml of a 1 wt % sodium hydroxide aqueous solution was added, and an aqueous layer was washed with chloroform twice and then acidified with a 5 wt % hydrochloric acid aqueous solution. A precipitated grey solid was collected by filtration under reduced pressure, washed with water and then dried under reduced pressure to give 10.3 g (yield 95%) of the title compound.

Workup

  1. temperaturewas heated at 110~110° C. for 6 hours
  2. distillationwas distilled off under reduced pressure
  3. temperatureThe mixture was refluxed
  4. temperatureunder heat for 2 hours
  5. temperatureto cool
  6. washan aqueous layer was washed with chloroform twice
  7. filtrationA precipitated grey solid was collected by filtration under reduced pressure
  8. washwashed with water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-950fd2bbdab846d0a42dc570eb3e4910
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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