Dimethylformamide → Ethyl p-[[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]thiomethyl]benzoate

HRID 1381599Notizen

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Reaktionsgleichung von HRID 1381599
[C:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][S:9][C:10]2[S:11][C:12]([SH:15])=[N:13][N:14]=2)=[C:6]([CH2:18][CH2:19][CH3:20])[C:5]=1[OH:21])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Br[CH2:34][C:35]1[CH:45]=[CH:44][C:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:37][CH:36]=1>C1(C)C=CC=CC=1>[C:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][S:9][C:10]2[S:11][C:12]([S:15][CH2:34][C:35]3[CH:45]=[CH:44][C:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:37][CH:36]=3)=[N:13][N:14]=2)=[C:6]([CH2:18][CH2:19][CH3:20])[C:5]=1[OH:21])(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 954261Ethyl 4-(bromomethyl)benzoateHCID 178439538HCID 178439538, Verbindung

Produkt 1

HCID 14839462Ethyl p-[[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]thiomethyl]benzoateAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of 340 mg of 2-[(4-acetyl-3-hydroxy-2propylbenzyl)thio]-5-mercapto-1,3,4-thiadiazole, 150 mg of anhydrous potassium carbonate and 5 ml of N,N-dimethylformamide was added 220 mg of ethyl p-(bromomethyl)benzoate followed by stirring at room temperature for 3 hours. The reaction mixture was diluted with 30 ml of toluene. After washing with water and drying over anhydrous magnesium sulfate, the system was concentrated under reduced pressure. The residue was applied to silica gel column chromatography. Elution with a mixture of toluene-ethyl acetate (9:1) gave 0.38 g of oily ethyl p-[[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]thiomethyl]benzoate.

Aufarbeitung

  1. washAfter washing with water
  2. dry with materialdrying over anhydrous magnesium sulfate
  3. concentrationthe system was concentrated under reduced pressure
  4. washElution
  5. additionwith a mixture of toluene-ethyl acetate (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-b2d6e92befe34512a90cf26164f6073f
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04803211

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