Borane;tetrahydrofuran → 6-Nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine

HRID 1618642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1618642
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[S:8][CH2:9][C:10](=O)[NH:11][C:6]=2[CH:5]=1)([O-:3])=[O:2].B.C1COCC1>>[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[S:8][CH2:9][CH2:10][NH:11][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Komponenten

3

Edukt 2

HCID 2723981Borane;tetrahydrofuranHCID 41823566-Nitro-2H-benzo[b][1,4]thiazin-3(4H)-one

Produkt 1

HCID 457916016-Nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine

Versuchsvorschrift

6-nitro-2H-benzo[b][1,4]thiazin-3(4H)-one (4 g, 19 mmol) was stirred in BH3-THF (285 mL, 258 mmol) at reflux overnight. After this time the reaction mixture was cooled to rt and quenched with MeOH. The reaction was partitioned between EtOAc and water. The separated organic layer was dried over Mg2SO4 and evaporated in vacuo to give 6-nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine that was used without further purification in the next step. Mass Spectrum (ESI) m/e=197 (M+1).

Aufarbeitung

  1. temperatureat reflux overnight
  2. customquenched with MeOH
  3. customThe reaction was partitioned between EtOAc and water
  4. dry with materialThe separated organic layer was dried over Mg2SO4
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-09883a05e25f434c859cd510e68e29cd
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765940B2

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