Bis(trimethylsilyl)carbodiimide → N-(6-bromochroman-4-ylidene)cyanamide

HRID 2096514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2096514
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[O:8][CH:7](C1C=CC=CC=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:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=[N:26][C:20]#[N:21]

Komponenten

5

Edukt 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 584240016-Bromo-7-fluoro-2-phenylchroman-4-one

Produkt 1

HCID 58424110N-(6-bromochroman-4-ylidene)cyanamideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 6-bromo-7-fluoro-2-phenylchroman-4-one (289.3 mg, 1.28 mmol) in DCM (10 mL) was added TiCl4 (2.6 mL, 1 M in CH2Cl2) dropwise within 15 minutes at room temperature. After stirring for 1 h, N,N′-methanediylidenebis(1,1,1-trimethylsilanamine) (0.63 mL, 2.82 mmol) was added dropwise. The mixture was stirred at room temperature overnight and poured into ice-water (50 g). The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic layer was dried and concentrated to give crude N-(6-bromochroman-4-ylidene)cyanamide (300 mg, 94%).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. customThe combined organic layer was dried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-775ce787c82842a4bd05cfdf2521fa53
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450308B2

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