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Triethylamine → HCID 14850389, Verbindung

HRID 973827
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 973827
C(N(CC)CC)C.[C:8]1([C:14]([NH:27][C:28]2[S:29][CH:30]=[C:31](/[C:33](=[N:37]/[OH:38])/[C:34]([OH:36])=[O:35])[N:32]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:39]1[O:50][C:49]2[CH:48]=[CH:47][C:43]([C:44](Cl)=[O:45])=[CH:42][C:41]=2[O:40]1>ClCCl>[C:8]1([C:14]([NH:27][C:28]2[S:29][CH:30]=[C:31](/[C:33](=[N:37]/[O:38][C:44](=[O:45])[C:43]3[CH:47]=[CH:48][C:49]4[O:50][CH2:39][O:40][C:41]=4[CH:42]=3)/[C:34]([OH:36])=[O:35])[N:32]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 11732720HCID 11732720, Verbindung

Produkt 1

HCID 14850389HCID 14850389, VerbindungAusbeute 21,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Triethylamine (6.7 ml) was added with stirring to an ice-cooled suspension of 10 g of 2-(2-triphenylmethylamino-4-thiazolyl)-2-(Z-hydroxyimino)acetic acid in 140 ml of anhydrous dichloromethane. The suspension turned to a clear, faint yellow solution after ten minutes. A solution of 3,4-methylenedioxybenzoyl chloride (3.4 g) in 25 ml of dichloromethane was dropwise added and the mixture was stirred at room temperature for one hour. The insoluble crystals were removed by filtration and the filtrate was washed twice with 20 ml of 1N hydrochloric acid and 30 ml of saturated sodium chloride solution each, and dried over anhydrous sodium sulfate. The dried filtrate was concentrated under reduced pressure, and the viscous brown residue (14.2 g) was purified by silica gel column chromatography using chloroform/methanol (20-10:1) as eluent, affording 2.3 g of the objective compound as light brown crystals.

Aufarbeitung

  1. temperaturecooled
  2. customafter ten minutes
  3. customThe insoluble crystals were removed by filtration
  4. washthe filtrate was washed twice with 20 ml of 1N hydrochloric acid and 30 ml of saturated sodium chloride solution each, and
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe dried filtrate was concentrated under reduced pressure
  7. customthe viscous brown residue (14.2 g) was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9ab54042d5bc4f2bae73fbf4ba1ee8a0
Quelldatensatz
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05064953

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