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Hydrochloric Acid → 2-{4-[2-(2-Nitrophenyl)-vinyl]-phenyl}-6-methoxybenzothiazole

HRID 339489
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 339489
[O:1]([C:3]1[CH:26]=[CH:25][C:6]2[N:7]=[C:8]([C:10]3[CH:24]=[CH:23][C:13]([CH2:14]P(=O)(OCC)OCC)=[CH:12][CH:11]=3)[S:9][C:5]=2[CH:4]=1)[CH3:2].[N+:27]([C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH:32]=O)([O-:29])=[O:28].C[O-].[Na+].Cl>CO.O>[N+:27]([C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH:32]=[CH:14][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[S:9][C:5]3[CH:4]=[C:3]([O:1][CH3:2])[CH:26]=[CH:25][C:6]=3[N:7]=2)=[CH:24][CH:23]=1)([O-:29])=[O:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 111012-NitrobenzaldehydeHCID 10942334Sodium MethoxideHCID 13599215Diethyl 4-(6-methoxybenzothiazol-2-yl)benzylphosphonate

Produkt 1

HCID 672367122-{4-[2-(2-Nitrophenyl)-vinyl]-phenyl}-6-methoxybenzothiazoleAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of diethyl 4-(6-methoxylbenzothiazol-2-yl)benzylphosphonate (0.10 g, 0.25 mmol) and 2-nitrobenzaldehyde (0.39 g, 0.25 mmol) in dry MeOH (10 ml) at 0° C. was added dropwise a solution of 0.5 M sodium methoxide (1.02 ml, 0.51 mmol). The reaction mixture was then allowed to rise to room temperature and heated under reflux for 18 h. The reaction mixture was cooled to room temperature and water (30 ml) was added followed by 1 M HCl until the reaction mixture became acidic. The reaction mixture was then extracted with DCM (3×80 ml) and the combined organic extracts washed with brine (50 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give a solid which was purified by flash chromatography (DCM) to give the title compound (0.043 g, 43%) as a yellow solid.

Aufarbeitung

  1. customto rise to room temperature
  2. temperatureheated
  3. temperatureunder reflux for 18 h
  4. extractionThe reaction mixture was then extracted with DCM (3×80 ml)
  5. washthe combined organic extracts washed with brine (50 ml)
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was removed under reduced pressure
  8. customto give a solid which
  9. customwas purified by flash chromatography (DCM)

Quellen und Nachweise

ORD-Eintrag
ord-bf730d2810124dec845a7553130dedc8
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08895313B2

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