Water → 4-[(1,3-Dithian-2-ylidene)(phenyl)methyl]-N,N-dimethylaniline

HRID 1708997

Reaktionsgleichung

Reaktionsgleichung von HRID 1708997
C[Si](C)(C)[CH:3]1[S:8][CH2:7][CH2:6][CH2:5][S:4]1.C([Li])CCC.[CH3:16][N:17]([CH3:32])[C:18]1[CH:31]=[CH:30][C:21]([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=O)=[CH:20][CH:19]=1.O>O1CCCC1.CCCCCC.ClCCl>[CH3:32][N:17]([CH3:16])[C:18]1[CH:31]=[CH:30][C:21]([C:22](=[C:3]2[S:8][CH2:7][CH2:6][CH2:5][S:4]2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 107374-(Dimethylamino)benzophenoneHCID 834132-Trimethylsilyl-1,3-dithianeHCID 178418339Butyllithium

Produkt 1

HCID 133019974-[(1,3-Dithian-2-ylidene)(phenyl)methyl]-N,N-dimethylaniline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

There is added to a solution of 2-trimethylsilyl-1,3-dithiane (16.2 g ) in dry tetrahydrofuran (170 ml) at -65° a 1.9M solution of n-butyllithium in hexane (45 ml). The reaction mixture is progressively warmed to 0° in the course of 31/2 hours and cooled to -65°. A solution of 4-dimethylamino-benzophenone (19.2 g) in dry tetrahydrofuran (100 ml) is than slowly added. The reaction mixture is progressively warmed to room temperature overnight and poured into a mixture of water (1000 ml ) and dichloromethane (200 ml). After separation of the layers, the aqueous solution is extracted with dichloromethane (3×200 ml). The combined organic solutions are washed with water (100 ml) and dried over magnesium sulphate. The solvents are evaporated in vacuo and the residue is recrystallised from ethyl acetate. The product is dried in vacuo to constant weight to yield (4-dimethylaminophenyl)(1,3-dithian-2-ylidene)-phenylmethane, m.p. 172°-174°.

Aufarbeitung

  1. temperaturecooled to -65°
  2. additionthan slowly added
  3. customAfter separation of the layers
  4. extractionthe aqueous solution is extracted with dichloromethane (3×200 ml)
  5. washThe combined organic solutions are washed with water (100 ml)
  6. dry with materialdried over magnesium sulphate
  7. customThe solvents are evaporated in vacuo
  8. customthe residue is recrystallised from ethyl acetate
  9. customThe product is dried in vacuo to constant weight

Quellen und Nachweise

ORD-Eintrag
ord-46024b1f7ed94f84adbec3203a3b2645
Quelldatensatz
uspto-grants-1990_08
Patentnummer
US04946861

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