Bromine → N2-Mesityl-4-methyl-N7,N7-dipropyl-1,3-benzothiazole-2,7-diamine

HRID 2235509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2235509
[CH2:1]([N:4]([CH2:25][CH2:26][CH3:27])[C:5]1[CH:6]=[CH:7][C:8]([CH3:24])=[C:9]([NH:11][C:12]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])=[S:13])[CH:10]=1)[CH2:2][CH3:3].BrBr>C(Cl)(Cl)(Cl)Cl.O>[C:20]1([CH3:21])[CH:19]=[C:18]([CH3:22])[CH:17]=[C:16]([CH3:23])[C:15]=1[NH:14][C:12]1[S:13][C:10]2[C:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:25][CH2:26][CH3:27])=[CH:6][CH:7]=[C:8]([CH3:24])[C:9]=2[N:11]=1

Komponenten

5

Edukt 2

HCID 24408BromineHCID 866129911-(5-Dipropylamino-2-methylphenyl)-3-mesitylthiourea

Produkt 1

HCID 58896415N2-Mesityl-4-methyl-N7,N7-dipropyl-1,3-benzothiazole-2,7-diamineAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittel2×

Versuchsvorschrift

To a mixture of 1-(5-dipropylamino-2-methylphenyl)-3-mesitylthiourea (100 mg, 0.261 mmol) in carbon tetrachloride (10 ml) was added dropwise bromine (0.015 ml, 0.287 mmol) in carbon tetrachloride (5 ml) over 30 min. The mixture was refluxed for 18 h and diluted with water. The aqueous solution was extracted with dichloromethane. The extract was washed with water and brine and concentrated under vacuum. The residue was purified by chromatography eluting with 10% AcOEt in n-hexane to afford 39 mg of the title compound.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 18 h
  2. extractionThe aqueous solution was extracted with dichloromethane
  3. washThe extract was washed with water and brine
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by chromatography
  6. washeluting with 10% AcOEt in n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-a6e937661b2343fe881f9151477098c8
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07714009B2

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