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Water → N-(10-methoxymethyl-10H-Pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl) chloro-acetamide

HRID 1059371
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1059371
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[N:8]([CH2:16][O:17][CH3:18])[C:7]=2[CH:19]=1.C(N(CC)CC)C.[Cl:27][CH2:28][C:29](Cl)=[O:30].O>CN(C)C=O.ClCCl>[CH3:18][O:17][CH2:16][N:8]1[C:7]2[CH:19]=[C:3]([CH2:2][NH:1][C:29](=[O:30])[CH2:28][Cl:27])[CH:4]=[CH:5][C:6]=2[S:11][C:10]2[N:12]=[CH:13][CH:14]=[N:15][C:9]1=2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 186704238-aminomethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

Produkt 1

HCID 23565184N-(10-methoxymethyl-10H-Pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl) chloro-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.25 g of 8-aminomethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine and 0.7 ml of triethylamine were dissolved in N,N-dimethylformamide (15 ml). Under ice-cooling, 2 ml of a solution of 0.4 ml of chloroacetyl chloride in dichloromethane was dropped thereinto and the resulting mixture was stirred for 1 hour. After adding water, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After concentrating under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate). The crystals thus obtained were washed with n-hexane and thus 1.28 g of the title compound was obtained as a yellow powder.

Aufarbeitung

  1. temperatureUnder ice-cooling
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
  5. concentrationAfter concentrating under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)
  7. customThe crystals thus obtained
  8. washwere washed with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-f6608daa2c554987a8f6fd222c3cb18a
Quelldatensatz
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06518423B1

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