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Bromine → 5-Bromo-1,3-benzothiazol-2-amine

HRID 2378559
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2378559
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH2:11])=[S:10])[CH:5]=[CH:6][CH:7]=1.BrBr>C(Cl)(Cl)Cl>[NH2:11][C:9]1[S:10][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[N:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 24408BromineHCID 2735619(3-Bromophenyl)thiourea

Produkt 1

HCID 137757855-Bromo-1,3-benzothiazol-2-amineAusbeute 47,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

A solution of Intermediate 74 (1.29 g) in chloroform (12 ml) was added dropwise with a solution of bromine (272 μl, WAKO) in chloroform (1.5 ml), refluxed by heating for 2.5 hours, and stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, neutralized with 5% aqueous ammonia, and then added with water (50 ml) and methylene chloride (150 ml) for extraction. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1) to obtain the title compound (Intermediate 75, 609 mg).

Aufarbeitung

  1. temperaturerefluxed
  2. temperatureby heating for 2.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionadded with water (50 ml) and methylene chloride (150 ml) for extraction
  5. customThe organic layer was dried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-80846b5db6684b528ad62e2bf20204d4
Quelldatensatz
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07470807B2

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