Ethyl 4-chlorobutyrate → 3-Acetyl-2-[2-[3-(ethoxycarbonyl)-propoxy]phenyl]benzothiazoline

HRID 1583664

Reaktionsgleichung

Reaktionsgleichung von HRID 1583664
[H-].[Na+].[C:3]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8][CH:7]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])(=[O:5])[CH3:4].Cl[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C=O)C>[C:3]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8][CH:7]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])(=[O:5])[CH3:4]

Komponenten

5

Edukt 3

HCID 18474Ethyl 4-chlorobutyrateHCID 24758Sodium hydrideHCID 133359603-Acetyl-2-(2-hydroxyphenyl)benzothiazoline

Produkt 1

HCID 135642173-Acetyl-2-[2-[3-(ethoxycarbonyl)-propoxy]phenyl]benzothiazoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To the suspension of 1.59 g of sodium hydride in 30 ml of anhydrous DMF, the solution of 8.13 g of 3-acetyl-2-(2-hydroxyphenyl)benzothiazoline in 30 ml of anhydrous DMF is added dropwise under nitrogen atmosphere at room temperature. After the addition, the reaction mixture is stirred for 20 minutes at room temperature. To the reaction mixture, the solution of 4.95 g of ethyl 4-chlorobutyrate in 15 ml of anhydrous DMF is added and stirred for 5 hours at 70° C. After cooling to room temperature the reaction mixture is poured into ice-water and extracted with ethyl acetate.

Aufarbeitung

  1. additionAfter the addition
  2. stirringstirred for 5 hours at 70° C
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. extractionextracted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ea80df91050c433e9257b2fc0681b9cb
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04552969

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