Sodium hydride → 3-Acetyl-2-[2-(3-dimethylaminopropoxy)phenyl]benzothiazoline

HRID 637752

Reaktionsgleichung

Reaktionsgleichung von HRID 637752
[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].[CH3:22][N:23]([CH3:28])[CH2:24][CH2:25][CH2:26]Cl>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][CH2:26][CH2:25][CH2:24][N:23]([CH3:28])[CH3:22])(=[O:5])[CH3:4]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 133359603-Acetyl-2-(2-hydroxyphenyl)benzothiazoline

Produkt 1

HCID 133357593-Acetyl-2-[2-(3-dimethylaminopropoxy)phenyl]benzothiazolineAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To the suspension of 0.26 g of the sodium hydride in anhydrous DMF, the solution of 1.36 g of 3-acetyl-2-(2-hydroxyphenyl)benzothiazoline in 5 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 0.61 g of 3-dimethylaminopropyl chloride in 10 ml of anhydrous DMF is added. The reaction mixture is stirred for 2 hours at 80° C., and washed with n-hexane after cooling and poured into ice-water. The separated oil is extracted with ethyl acetate. The organic layer is washed with N--NaOH solution, water and saturated sodium chloride solution in the order named and dried over anhydrous magnesium sulfate. Ethy acetate is removed off in vacuo to give 1.0 g (56%) of the titled compound.

Aufarbeitung

  1. additionAfter the addition
  2. stirringThe reaction mixture is stirred for 2 hours at 80° C.
  3. washwashed with n-hexane
  4. temperatureafter cooling
  5. additionpoured into ice-water
  6. extractionThe separated oil is extracted with ethyl acetate
  7. washThe organic layer is washed with N
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customEthy acetate is removed off in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2bc37b56090748659ea5ce9af168942d
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04558125

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