3-Nitrophenylboronic Acid → 7-(3-nitro-phenyl)-4H-benzo[1,4]thiazin-3-one

HRID 2230042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2230042
Br[C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][S:9][C:4]=2[CH:3]=1.[N+:13]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14].C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.C(O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+:13]([C:16]1[CH:21]=[C:20]([C:2]2[CH:12]=[CH:11][C:5]3[NH:6][C:7](=[O:10])[CH2:8][S:9][C:4]=3[CH:3]=2)[CH:19]=[CH:18][CH:17]=1)([O-:15])=[O:14]

Komponenten

8

Edukt 3

HCID 16773-Nitrophenylboronic AcidHCID 11430Potassium CarbonateHCID 6890657-Bromo-2H-(1,4)-benzothiazin-3(4h)-one

Produkt 1

HCID 98823337-(3-nitro-phenyl)-4H-benzo[1,4]thiazin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of 7-bromo-4H-benzo[1,4]thiazin-3-one (2 g, 8.2 mmol), 3-nitrophenyl boronic acid (2.72 g, 16.4 mmol), potassium carbonate (6.85 g, 49.2 mmol), and tetrakis(triphenylphosphine) palladium(0) (0.95 g, 0.82 mmol) in dimethoxyethane (100 ml), ethanol (25 ml), and water (25 ml) was heated to reflux for 6 hours. After cooling to room temperature, the mixture was diluted with water and extracted with EtOAc (3×50 mL). The combined organic extracts were washed with water, then brine, dried (MgSO4) and evaporated to obtain crude 7-(3-nitro-phenyl)-4H-benzo[1,4]thiazin-3-one (0.15 g, 6%). Recrystallization of crude sample from EtOAc afforded the title compound: mp 290-292° C.; MS (EI) m/z 286 (M+).

Aufarbeitung

  1. temperatureto reflux for 6 hours
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic extracts were washed with water
  4. dry with materialbrine, dried (MgSO4)
  5. customevaporated
  6. customto obtain crude 7-(3-nitro-phenyl)-4H-benzo[1,4]thiazin-3-one (0.15 g, 6%)
  7. customRecrystallization of crude sample from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-e3fca2e5a76341cd83850bf25c3e34af
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06423699B1

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