Bis(trimethylsilyl)carbodiimide → N-(7-bromo-3-phenyl-3,4-dihydrobenzo[b]oxepin-5(2H)-ylidene)cyanamide

HRID 1408795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1408795
[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[O:6][CH2:7][CH:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:9][C:10](=O)[C:4]=2[CH:3]=1.[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:19]=[CH:18][C:5]2[O:6][CH2:7][CH:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:9][C:10](=[N:26][C:20]#[N:21])[C:4]=2[CH:3]=1

Komponenten

5

Edukt 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 584241057-bromo-3-phenyl-3,4-dihydrobenzo[b]oxepin-5(2H)-one

Produkt 1

HCID 58424178N-(7-bromo-3-phenyl-3,4-dihydrobenzo[b]oxepin-5(2H)-ylidene)cyanamideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 7-bromo-3-phenyl-3,4-dihydrobenzo[b]oxepin-5(2H)-one (158 mg, 0.5 mmol) in DCM (5 mL) was added TiCl4 (1 mL, 1 M in CH2Cl2) dropwise within 15 minutes at room temperature. After stirring for 1 h, N,N′-methanediylidenebis(1,1,1-trimethylsilanamine) (0.25 mL, 1.11 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-(7-bromo-3-phenyl-3,4-dihydrobenzo[b]oxepin-5(2H)-ylidene)cyanamide (160 mg, 94%).

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-be6a835e54fe438aa68b38dc07c840b5
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921359B2

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