Bis(trimethylsilyl)carbodiimide → N-(5'-(3-chloro-5-fluorophenyl)-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-ylidene)cyanamide

HRID 1503417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1503417
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]4([CH2:22][CH2:21][C:20]5[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=5[CH2:18][CH2:17]4)[C:14](=O)[C:13]=3[CH:28]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.C[Si]([N:33]=[C:34]=[N:35][Si](C)(C)C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]4([CH2:22][CH2:21][C:20]5[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=5[CH2:18][CH2:17]4)[C:14](=[N:35][C:34]#[N:33])[C:13]=3[CH:28]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Komponenten

5

Edukt 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 581980625'-(3-chloro-5-fluorophenyl)-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-one

Produkt 1

HCID 86652173N-(5'-(3-chloro-5-fluorophenyl)-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-ylidene)cyanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 5′-(3-chloro-5-fluorophenyl)-5,6,8,9-tetrahydro-3′H-spiro[benzo[7]annulene-7,2′-benzofuran]-3′-one (0.0607 g, 0.155 mmol) in CH2Cl2 (5 mL) was added 0.7 mL of 1.0 M TiCl4 in CH2Cl2 at room temperature. After 1 h, 0.28 mL of bis(trimethylsilyl)carbodiimide was added to the red solution. The resulting mixture was then stirred at room temperature for 18 h. The mixture was quenched with ice, diluted with CH2Cl2, and dried over Na2SO4. After the solvent was removed under reduced pressure, the crude product was directly used in the next step without further purification.

Aufarbeitung

  1. customThe mixture was quenched with ice
  2. additiondiluted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. customAfter the solvent was removed under reduced pressure
  5. customthe crude product was directly used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-44d9d81e0ddc4bd0bb3e2a416c8b881e
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212153B2

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