Oxalyl chloride → (Z)-5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylmethyl isocyanate

HRID 2371483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2371483
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21]C(O)=O.[C:25](Cl)(=[O:29])C(Cl)=O.C[Si]([N:35]=[N+]=[N-])(C)C>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][N:35]=[C:25]=[O:29]

Komponenten

6

Edukt 3

HCID 65578Oxalyl chlorideHCID 78378AzidotrimethylsilaneHCID 5352624Sulindac Sulfide

Produkt 1

HCID 86745524(Z)-5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylmethyl isocyanate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of (Z)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylacetic acid (5.0 g, 14.7 mmol) in methylene chloride (50 mL) at room temperature there was added oxalyl chloride (2.8 g, 22 mmol) and DMF (2 drops) and the mixture stirred for 1 hour; the solution was evaporated and the crude acid chloride flushed twice with carbon tetrachloride (20 mL) then suspended in carbon tetrachloride (25 mL) and trimethylsilyl azide (2.53 g, 22 mmol) was added. The mixture was stirred at room temperature for 15 minutes, then gently heated on a steam bath as nitrogen was evolved. The heating was continued until gas evolution ceased, then the mixture was evaporated to afford the crude title compound as an oil which was used as such in the next step.

Aufarbeitung

  1. customthe solution was evaporated
  2. customthe crude acid chloride flushed twice with carbon tetrachloride (20 mL)
  3. stirringThe mixture was stirred at room temperature for 15 minutes
  4. temperaturegently heated on a steam bath as nitrogen
  5. customthe mixture was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-10469a19dbdf4a6ca229c58a323534be
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05093356

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