Methanol → HCID 53807098, compound

HRID 1871633Notes

Reaction equation

HRID 1871633 reaction equation
[OH-].[Na+].[C:3]1([S:9][CH:10]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][O:25][N:26]=[C:27]([C:29]3[CH:34]=[CH:33][C:32]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)=[CH:31][CH:30]=3)[CH3:28])=[CH:18][CH:17]=2)[C:11]([O:13]C)=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CO>O1CCOCC1>[C:3]1([S:9][CH:10]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][O:25][N:26]=[C:27]([C:29]3[CH:30]=[CH:31][C:32]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)=[CH:33][CH:34]=3)[CH3:28])=[CH:18][CH:17]=2)[C:11]([OH:13])=[O:12])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 53761508HCID 53761508, compound

Product 1

HCID 53807098HCID 53807098, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

2.00 ml of a 1N aqueous sodium hydroxide solution was added to a mixture of 350 mg of methyl 2-phenylthio-3-[4-[2-[[1-[4(2-pyridyl)phenyl]ethylidene]aminoxy]ethoxy]phenyl]propionate obtained in Example 3, 3 ml of methanol and 2 ml of dioxane, and the mixture was stirred at 50° C. for 4 hours. After the reaction, the reaction mixture was concentrated and diluted with water. Then, the pH of the reaction mixture was adjusted to a value of 3 with 1N hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated to obtain 324 mg of the desired compound as a foamy solid.

Workup

  1. customAfter the reaction
  2. concentrationthe reaction mixture was concentrated
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2dabec0556dc4e8a9a71d1fa7856085f
Source dataset
uspto-grants-2000_08
Patent number
US06103907

Reaction notes

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