Tributylvinyltin → 2-Diethylphosphonomethyloxy-5-vinylnitrobenzene
Reaktionsgleichung
[CH2:1]([O:3][P:4]([CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[CH2:21]([Sn](CCCC)(CCCC)C=C)[CH2:22]CC>CN(C=O)C.[Cl-].[Cl-].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.[Pd+2]>[CH2:1]([O:3][P:4]([CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:21]=[CH2:22])=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
A solution of 2-diethylphosphonomethyloxy-5-bromonitrobenzene (1 mmole, prepared as in Example 31, Step A from 2-fluoro-5-bromonitrobenzene) in DMF (5 mL) was treated with tributyl(vinyl)tin (1.2 mmole) and palladium bis(triphenylphosphine) dichloride (0.1 mmole), and the mixture was heated at 60° C. under nitrogen for 6 h. Evaporation and chromatography gave 2-diethylphosphonomethyloxy-5-vinylnitrobenzene as an oil which was subjected to Step B of Example 31, Step B of Example 29, and Step D of Example 27 to give 2-amino-7-ethyl-6-thiocyano-4-phosphonomethoxybenzothiazole (34.1). mp>167° C.(dec.). Anal. calcd. for C11H12N3O4PS2: C: 38.26; H: 3.50; N: 12.17. Found: C: 37.87; H: 3.47; N: 11.93.
Aufarbeitung
- customEvaporation and chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-03b098aba5c84a6c8d079bfa12f73533
- Quelldatensatz
- uspto-grants-2005_11
- Patentnummer
- US06965033B2
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