1,1'-Azobis(cyclohexanecarbonitrile) → 1-Methanesulfonyl-5-chloro-spiro[indoline-3,3'-pyrrolidine]

HRID 2068505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2068505
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:13][C:14](=[CH2:20])[CH2:15][CH2:16][N:17]=[N+]=[N-])[S:9]([CH3:12])(=[O:11])=[O:10])=[C:4](I)[CH:3]=1.C[Si]([SiH]([Si](C)(C)C)[Si](C)(C)C)(C)C.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>C1C=CC=CC=1>[CH3:12][S:9]([N:8]1[C:5]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:14]2([CH2:15][CH2:16][NH:17][CH2:20]2)[CH2:13]1)(=[O:11])=[O:10]

Komponenten

5

Edukt 3

HCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 123134Tris(trimethylsilyl)silaneHCID 86627362N-(4-Chloro-2-iodo-phenyl)-N-(4-azido-2-methylene-butyl)-methanesulfonamide

Produkt 1

HCID 581373391-Methanesulfonyl-5-chloro-spiro[indoline-3,3'-pyrrolidine]Ausbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A degassed solution of N-(4-Chloro-2-iodo-phenyl)-N-(4-azido-2-methylene-butyl)-methanesulfonamide (1.38 g) in benzene (200 ml) was heated to reflux under argon. Tris(trimethylsilyl)silane (1.32 ml) was added dropwise followed by 1,1′-azobis(cyclohexane carbonitrile) (110 mg). The reaction mixture was stirred at reflux for 20 hours then concentrated in vacuo. The residue was dissolved in ethyl acetate (60 ml), extracted with HCl 2N (3×60 ml). The aqueous layer was basified with 2N sodium hydroxide (250 ml) then extracted with ethyl acetate (3×150 ml). The combined organic layers were dried over sodium sulfate and the solvent evaporated in vacuo to afford 1-methanesulfonyl-5-chloro-spiro[indoline-3,3′-pyrrolidine] (766 mg) which was used as such for the next step.

Aufarbeitung

  1. temperatureto reflux under argon
  2. temperatureat reflux for 20 hours
  3. concentrationthen concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (60 ml)
  5. extractionextracted with HCl 2N (3×60 ml)
  6. extractionthen extracted with ethyl acetate (3×150 ml)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. customthe solvent evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-528366a1f1e442c39576a2f8f1308c81
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299058B2

Notizen zur Reaktion

Wird geladen…