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Dimethylformamide → 2-(4-Benzyloxy-3-methoxyphenyl)benzothiazole

HRID 340659
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 340659
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=O)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.S(Cl)(Cl)=O.[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[SH:36]>C(Cl)Cl.N1C=CC=CC=1.O.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]2[S:36][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[N:29]=2)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 6228DimethylformamideHCID 87132-AminothiophenolHCID 24386Thionyl ChlorideHCID 2263354-(Benzyloxy)-3-methoxybenzoic acid

Produkt 1

HCID 669113302-(4-Benzyloxy-3-methoxyphenyl)benzothiazole

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962
Water
Lösungsmittel
2×
HCID 1049PyridineLösungsmittel
HCID 1140TolueneLösungsmittel2×
HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

In methylene chloride (10 ml) was suspended 2.0 g (7.7 mmol) of 4-benzyloxy-3-methoxy benzoic acid. To this suspension was added 0.05 g of DMF and 0.68 ml of thionyl chloride, followed by stirring at 50° C. for 2 hours. This reaction solution was introduced dropwise at 0° C. into a solution wherein 1.2 g (9.3 mmol) of 2-aminothiophenol had been dissolved in 10 ml of pyridine at room temperature. The mixture was further stirred overnight at room temperature, diluted with water, and subjected to ethyl acetate extraction (50 ml×2 times). The extracts were dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue thus obtained was dissolved in 30 ml of toluene. This toluene solution was heated to reflux overnight while water was distilled off. Toluene was removed from this solution by distillation under reduced pressure, and the residue was purified using a silica gel column (eluant:ethyl acetate/hexane=1/5). The solvent was distilled off under reduced pressure. Using the crystals thus obtained, the desired compound was recrystallized in an amount of 0.18 g from methylene chloride-hexane.

Aufarbeitung

  1. waitThe mixture was further stirred overnight at room temperature
  2. extractionsubjected to ethyl acetate extraction (50 ml×2 times)
  3. dry with materialThe extracts were dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue thus obtained
  6. distillationwas distilled off
  7. customToluene was removed from this solution by distillation under reduced pressure
  8. customthe residue was purified
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthus obtained
  11. customthe desired compound was recrystallized in an amount of 0.18 g from methylene chloride-hexane

Quellen und Nachweise

ORD-Eintrag
ord-601a2c7cf5f540bf80d41a7047f198a8
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08895599B2

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