Bis(trimethylsilyl)carbodiimide → N-(6-bromo-3'-isopropylspiro[chroman-2,1'-cyclopentane]-4-ylidene)cyanamide

HRID 2096553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2096553
[Br:1][C:2]1[CH:3]=[C:4]2[C:16](=[CH:17][CH:18]=1)[O:15][C:7]1([CH2:11][CH2:10][CH:9]([CH:12]([CH3:14])[CH3:13])[CH2:8]1)[CH2:6][C:5]2=O.[C:20](=[N:26][Si](C)(C)C)=[N:21][Si](C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:16](=[CH:17][CH:18]=1)[O:15][C:7]1([CH2:11][CH2:10][CH:9]([CH:12]([CH3:14])[CH3:13])[CH2:8]1)[CH2:6][C:5]2=[N:26][C:20]#[N:21]

Komponenten

5

Edukt 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 584237926-Bromo-3'-isopropylspiro[chroman-2,1'-cyclopentan]-4-one

Produkt 1

HCID 58424005N-(6-bromo-3'-isopropylspiro[chroman-2,1'-cyclopentane]-4-ylidene)cyanamideAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 6-bromo-3′-isopropylspiro[chroman-2,1′-cyclopentan]-4-one (250 mg, 0.776 mmol) in DCM (10 mL) was added TiCl4 (1.55 mL, 1 M in CH2Cl2) dropwise within 15 minutes at room temperature. After stirring for 1 h, N,N′-methanediylidenebis(1,1,1-trimethylsilanamine) (0.38 mL, 1.707 mmol) was added dropwise. The mixture was stirred at room temperature overnight and poured into ice-water (25 g). The aqueous layer was extracted with CH2Cl2, which was combined with the organic layer. The organic layer was dried and concentrated to give crude N-(6-bromo-3′-isopropylspiro[chroman-2,1′-cyclopentane]-4-ylidene)cyanamide (250 mg, 93%). 1H-NMR (CDCl3): 0.82 (m, 6H), 1.36 (m, 2H), 1.69 (m, 3H), 1.96 (m, 3H), 3.10 (d, 2H), 6.75 (m, 1H), 7.52 (m, 1H), 8.04 (d, 1H).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature overnight
  2. extractionThe aqueous layer was extracted with CH2Cl2, which
  3. customThe organic layer was dried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-178005d70cdb4489b5bb3e4843cca962
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450308B2

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