Isopropyl iodide → 6-nitro-3-isopropyl-2(3H)-benzothiazolone

HRID 1991260

Reaktionsgleichung

Reaktionsgleichung von HRID 1991260
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9](=[O:11])[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].N12CCCN=C1CC[CH2:17][CH2:16][CH2:15]2.IC(C)C>CN(C)C=O.O>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[N:8]([CH:16]([CH3:17])[CH3:15])[C:9](=[O:11])[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 3

HCID 6362Isopropyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6415712(3H)-Benzothiazolone, 6-nitro-

Produkt 1

HCID 218780606-nitro-3-isopropyl-2(3H)-benzothiazolone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A stirred solution of 6-nitro-2-benzothiazolinone (5.0 g, 25.5 mmol) in anhydrous N,N-dimethylformamide (51 mL) under N2 is treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (4.96 mL, 33.1 mmol) dropwise. Following a slight exotherm, the reaction mixture is heated up to 50° C. and treated with 2-iodopropane (12.7 mL, 127 mmol). The resulting mixture is quickly heated up to 75° C., stirred at this temperature for 40 mins, cooled to ambient temperature and diluted with ice (100 mL) and water (100 mL). The precipitate is isolated by filtration and recrystallized from ethyl acetate/hexanes to give the title compound, mp 138-142° C.

Aufarbeitung

  1. temperatureThe resulting mixture is quickly heated up to 75° C.
  2. temperaturecooled to ambient temperature
  3. customThe precipitate is isolated by filtration
  4. customrecrystallized from ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-70a6fd12212b4a8f86936b7a655ab0bd
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07645781B2

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