Ethyl Acetate → 7-Bromo-5-nitrobenzothiazole

HRID 380613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 380613
[N+:1]([C:4]1[C:5](N)=[C:6]([Br:13])[C:7]2[S:11][CH:10]=[N:9][C:8]=2[CH:12]=1)([O-:3])=[O:2].N(OS(=O)(=O)O)=O.O[PH2]=O.CCOC(C)=O>S(=O)(=O)(O)O>[N+:1]([C:4]1[CH:5]=[C:6]([Br:13])[C:7]2[S:11][CH:10]=[N:9][C:8]=2[CH:12]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 82157Nitrosylsulfuric acidHCID 4124402Phosphinic AcidHCID 227280347-Bromo-5-nitrobenzo[d]thiazol-6-amine

Produkt 1

HCID 227280317-Bromo-5-nitrobenzothiazoleAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 5-nitro-6-amino-7-bromobenzothiazole (1.0 g, 3.7 mmol) in 4 mL of sulfuric acid was added nitrososulfuric acid (1.2 g, 9.5 mmol) in a portion. The resulting reaction mixture was stirred for 12 h at 25° C. The reaction mixture was then cooled to 0° C. and 1 mL of H3PO2 was added into the solution. It was stirred for 12 h at another 25° C. and for 2 h at 50° C. The reaction mixture was then poured into EtOAc and washed with aq. NaHCO3. Organic layer was dried over Na2SO4 and concentrated in vacuo to provide an oil (0.85 g, 3.2 mmol, 89%), which was characterized as the desired product(>95% pure) and subjected to a following reaction without further purification.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. stirringIt was stirred for 12 h at another 25° C. and for 2 h at 50° C
  4. washwashed with aq. NaHCO3
  5. dry with materialOrganic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c3011ab581014581b8ca55f3bfe37049
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303643B1

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