2-Methoxypropene → 6-bromo-2,2-dimethyl-4-(1,3-dithian-2-yl)-2H-1,3-benzoxazine

HRID 326596

Reaktionsgleichung

Reaktionsgleichung von HRID 326596
C([Li])CCC.S1CCCSC1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([C:20]#[N:21])[CH:14]=1.[CH3:22][O:23][C:24]([CH3:26])=[CH2:25].[Br:27][C:28]1[CH:29]=[CH:30][C:31]2[O:36][C:35]([CH3:38])([CH3:37])[N:34]=[C:33]([CH:39]3[S:44][CH2:43][CH2:42][CH2:41][S:40]3)[C:32]=2[CH:45]=1>CCCCCC.O1CCCC1>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:25][CH:24]([O:23][CH3:22])[CH3:26])=[C:15]([CH:14]=1)[C:20]#[N:21].[Br:27][C:28]1[CH:29]=[CH:30][C:31]2[O:36][C:35]([CH3:37])([CH3:38])[N:34]=[C:33]([CH:39]3[S:40][CH2:41][CH2:42][CH2:43][S:44]3)[C:32]=2[CH:45]=1

Komponenten

9

Edukt 5

HCID 83002-MethoxypropeneHCID 104511,3-DithianeHCID 27570145-Bromo-2-hydroxybenzonitrileHCID 197350976-bromo-2,2-dimethyl-4-(1,3-dithian-2-yl)-2H-1,3-benzoxazineHCID 178418339Butyllithium

Produkt 2

HCID 197350976-bromo-2,2-dimethyl-4-(1,3-dithian-2-yl)-2H-1,3-benzoxazineHCID 197351265-Bromo-2-(2-methoxy-2-methylethoxy)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution (13.8 ml) of 1.6M n-butyllithium in hexane was added dropwise to a solution of 1,3-dithian (1.5 g) in anhydrous tetrahydrofuran (35 ml) at -78° C. under an argon atmosphere over 10 minutes. After stirring for 30 minutes, a solution of 5-bromo-2-(2-methoxy-2-methylethoxy)benzonitrile, which was prepared from 4-bromo-2-cyanophenol (m.p. 148°-150° C., 2.48 g) and 2-methoxypropene (1.1 g) according to the same manner as described in Example 29, in anhydrous tetrahydrofuran (5 ml) was added to the mixture. The mixture was treated in the same manner as that in Example 29 to obtain 6-bromo-2,2-dimethyl-4-(1,3-dithian-2-yl)-2H-1,3-benzoxazine (0.90 g) (Compound 105).

Aufarbeitung

  1. additionwas added to the mixture
  2. additionThe mixture was treated in the same manner as that in Example 29

Quellen und Nachweise

ORD-Eintrag
ord-30d90ac680874be6916d41865b13c04c
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05270308

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