3-Chloro-1,2-propanediol → 1-Fluoro-4-hydroxy-9H-thioxanthen-9-one

HRID 409528Notes

Reaction equation

HRID 409528 reaction equation
[F:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([OH:17])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:25][CH:26]([OH:29])[CH2:27][OH:28]>C(#N)C>[F:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([OH:17])=[CH:4][CH:3]=1.[OH:29][CH:26]([CH2:27][OH:28])[CH2:25][O:17][C:5]1[C:6]2[S:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14](=[O:16])[C:15]=2[C:2]([F:1])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 72903-Chloro-1,2-propanediolHCID 11430Potassium CarbonateHCID 136150131-Fluoro-4-hydroxy-9H-thioxanthen-9-one

Product 2

HCID 136150131-Fluoro-4-hydroxy-9H-thioxanthen-9-oneHCID 67285453HCID 67285453, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The reactant 1-fluoro-4-hydroxy-thioxanthen-9-one was prepared as described above in Example 1a. To a suspension of 1-fluoro-4-hydroxy-9H-thioxanthen-9-on (92%) (306 g, 1.14 mol) in acetonitrile (3500 mL), potassium carbonate (464 g, 3.36 mol) was added while stirring vigorously. 3-Chloro-1,2-propanediol (371 g, 3.36 mol) was added drop wise over 30 minutes. The reaction mixture was heated to reflux and allowed to stir for 24 hours. The mixture was filtered and the residue was washed with warm acetonitrile (500 mL) (70° C.). The filtrate was evaporated under reduced pressure. The residual solid was treated with a mixture of methyl-tert-butylether (400 mL) and acetone (40 ml) and stirred for about an hour. The crude 4-(2,3-dihydroxy-propoxy)-1-fluoro-thioxanthen-9-one was isolated by filtration and dried. The crude 4-(2,3-dihydroxy-propoxy)-1-fluoro-thioxanthen-9-one was treated twice with 1000 mL water at 60° C., isolated by filtration and dried.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. stirringto stir for 24 hours
  5. filtrationThe mixture was filtered
  6. washthe residue was washed with warm acetonitrile (500 mL) (70° C.)
  7. customThe filtrate was evaporated under reduced pressure
  8. additionThe residual solid was treated with a mixture of methyl-tert-butylether (400 mL) and acetone (40 ml)
  9. stirringstirred for about an hour

Sources & evidence

ORD record
ord-863891bedfcd45e19c2067e0b6ad5044
Source dataset
uspto-grants-2014_06
Patent number
US08759412B2

Reaction notes

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