Water → HCID 135590743, compound

HRID 1589727Notes

Reaction equation

HRID 1589727 reaction equation
[OH-].[K+].[CH2:3]([C:13]1[S:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24]C(=O)C)=[C:20]([F:28])[CH:19]=2)=[N:16][N:17]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O.S(=O)(=O)(O)O>C(O)C.CCCCCC>[CH2:3]([C:13]1[S:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([F:28])[CH:19]=2)=[N:16][N:17]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 19770592HCID 19770592, compound

Product 1

HCID 135590743HCID 135590743, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

1.59 g (24.1 mM) of 85%-potassium hydroxide was dissolved in 50 ml of ethanol on an oil bath (bath temperature: about 70° C.). To the solution, 3.37 g (wet, 8.90 mM) of 2-decyl-5-(4-acetoxy-3-fluorophenyl)-1,3,4-thiadiazole was added, followed by stirring for 10 minutes at about 70° C. After the reaction, the reaction mixture was poured into iced water, followed by filtration under reduced pressure. The filtrate was condensed, followed by successive addition of about 100 ml of water, 2.3 ml of concentrated sulfuric acid and common salt and stirring at room temperature to precipitate a crystal. The crystal was dissolved in ethyl acetate and dried with anhydrous sodium sulfuric acid. The sodium sulfuric acid was recovered by filtration and the filtrate was condensed into a solid; n-hexane was added to the solid and stirred at room temperature, followed by filtration to obtain 2.78 g of 2-decyl-5-(3-fluoro-4-hydroxyphenyl)-1,3,4-thiadiazole (Yield: 92.8%, Yield through the steps iii) and iv): 82.7%).

Workup

  1. customAfter the reaction
  2. filtrationfollowed by filtration under reduced pressure
  3. customcondensed
  4. stirringstirring at room temperature
  5. customto precipitate a crystal
  6. dissolutionThe crystal was dissolved in ethyl acetate
  7. dry with materialdried with anhydrous sodium sulfuric acid
  8. filtrationThe sodium sulfuric acid was recovered by filtration
  9. customcondensed into a solid
  10. stirringstirred at room temperature
  11. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-96b6fb6f72e24e36b70b43cd24d51583
Source dataset
uspto-grants-1993_04
Patent number
US05200109

Reaction notes

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