Methanol → Benzoic acid, 4-(((5-(((4-acetyl-3-hydroxy-2-propylphenyl)methyl)thio)-1,3,4-thiadiazol-2-yl)thio)methyl)-

HRID 1646524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1646524
[C:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][S:9][C:10]2[S:14][C:13]([S:15][CH2:16][C:17]3[CH:27]=[CH:26][C:20]([C:21]([O:23]CC)=[O:22])=[CH:19][CH:18]=3)=[N:12][N:11]=2)=[C:6]([CH2:30][CH2:31][CH3:32])[C:5]=1[OH:33])(=[O:3])[CH3:2].CO.O1CCCC1.[OH-].[Na+]>O>[C:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][S:9][C:10]2[S:14][C:13]([S:15][CH2:16][C:17]3[CH:27]=[CH:26][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)=[N:12][N:11]=2)=[C:6]([CH2:30][CH2:31][CH3:32])[C:5]=1[OH:33])(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 14839462Ethyl p-[[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]thiomethyl]benzoate

Produkt 1

HCID 3065384Benzoic acid, 4-(((5-(((4-acetyl-3-hydroxy-2-propylphenyl)methyl)thio)-1,3,4-thiadiazol-2-yl)thio)methyl)-Ausbeute 27,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 380 mg of ethyl p-[(5-[(4-acetyl-3-hydroxy-2-propylbenzyl )thio]-1,3,4-thiadiazol -2-yl)thiomethyl]benzoate, 2 ml of methanol, 2 ml of tetrahydrofuran and 2 ml of a 1N aqueous sodium hydroxide solution was stirred at 60° to 70° C. for 1 hour. After cooling, 20 ml cf water was added to the reaction mixture. The system was washed with ethyl acetate, made acidic with dil. hydrochloric acid and then, extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was recrystallized from isopropyl alcohol-water to give 100 mg of p-[[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]thiomethyl]benzoic acid. The physical property of the thus obtained compound was identical with that of the compound obtained in Example 37.

Aufarbeitung

  1. temperatureAfter cooling
  2. additionwas added to the reaction mixture
  3. washThe system was washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from isopropyl alcohol-water

Quellen und Nachweise

ORD-Eintrag
ord-2c8e09bb64f04823ae11349504915f33
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05180730

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