Potassium Hydroxide → HCID 68642113, compound

HRID 1498947Notes

Reaction equation

HRID 1498947 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:10][C:11]([C:15](=[O:17])[CH3:16])=[C:12]([CH3:14])[N:13]=1.[OH-:18].[K+].[C:20](O)(=[O:22])C.[C:24](O)(=O)C.IC1C=CC=CC=1>CO>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:10][C:11]([C:15]([O:22][CH3:20])([O:17][CH3:24])[CH2:16][OH:18])=[C:12]([CH3:14])[N:13]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 9344223HCID 9344223, compoundHCID 12217721Iodo benzene diacetate

Product 1

HCID 68642113HCID 68642113, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To methanol (5 ml), 1-[2-(2,4-dimethylphenyl)-4-methylthiazol-5-yl]ethanone (981 mg) prepared in the Step 31-1-1 was added, and a solution of potassium hydroxide (673 mg) in methanol (10 ml) was added dropwise thereto under cooling by ice and stirring. Thereafter, iodobenzene diacetate (1.42 g) was added to the mixture, and then the resulting mixture was stirred at a room temperature for 22 hours. From the mixture methanol was distilled off under a reduced pressure, and water was added to the residue. The resulting mixture was subjected to extraction with dichloromethane. The extract was dried over anhydrous sodium sulfate, and then dichloromethane was distilled off under a reduced pressure. Hexane was added to the residue, the precipitate was separated by filtration, washed with hexane, and then dried under a reduced pressure to give the title compound (328 mg, 26%).

Workup

  1. additionwas added
  2. temperatureunder cooling by ice
  3. stirringthe resulting mixture was stirred at a room temperature for 22 hours
  4. distillationFrom the mixture methanol was distilled off under a reduced pressure, and water
  5. additionwas added to the residue
  6. extractionThe resulting mixture was subjected to extraction with dichloromethane
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. distillationdichloromethane was distilled off under a reduced pressure
  9. additionHexane was added to the residue
  10. customthe precipitate was separated by filtration
  11. washwashed with hexane
  12. customdried under a reduced pressure

Sources & evidence

ORD record
ord-d6869d1da192415f8c5108dc5483b6d5
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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