Triphenylphosphine → 1-(7-Vinyl-2-benzothiazolyl)-3-ethylurea

HRID 9123

Reaktionsgleichung

FC(F)(F)S([C:6]1[C:14]2[S:13][C:12]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])=[N:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)(=O)=O.[Cl-].[Li+].[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:26]=1.C([Sn](C=C)(C=C)C=C)=C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:25]([C:6]1[C:14]2[S:13][C:12]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])=[N:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)=[CH2:26]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Similar to the synthesis of Example 203, a mixture of 1-(7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea (0.050 g, 80% pure, 0.11 mmol), lithium chloride (0.039 g, 0.92 mmol, 8.4 eq), triphenylphosphine (0.017 g, 0.066 mmol, 0.6 eq), Pd(PPh3)2Cl2 (0.009 g, 0.013 mmol, 0.12 eq), tetravinyltin (0.040 mL, 0.22 mmol, 2.0 eq), and a crystal of 2,6-di-tert-butyl-4-methylphenol was purged with nitrogen gas, and was heated at about 100° C. for about 1.5 hours. The mixture was taken up in MeOH, filtered, concentrated, and purified by HPLC and preparative TLC in ethyl acetate/heptane mixture to obtain 0.004 g (14%) of the desired compound. LC/MS 248 (M+1); LC retention time 2.96 min.

Aufarbeitung

customSimilar to the synthesis of Example 203
customa crystal of 2,6-di-tert-butyl-4-methylphenol was purged with nitrogen gas
filtrationfiltered
concentrationconcentrated
custompurified by HPLC and preparative TLC in ethyl acetate/heptane mixture

Quellen und Nachweise

ORD-Eintrag: ord-1b2a9a1d73d34afbbad146c0399680cb
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07091227B2

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