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

HRID 472969ノート

反応式

HRID 472969 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]3([CH2:15][CH2:14][C:13]4[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=4[CH2:11][CH2:10]3)[C:7](=O)[C:6]=2[CH:21]=1.C[Si](C)(C)[N:24]=[C:25]=[N:26][Si](C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]3([CH2:15][CH2:14][C:13]4[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=4[CH2:11][CH2:10]3)[C:7](=[N:26][C:25]#[N:24])[C:6]=2[CH:21]=1

参加物

5

反応物 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 581970305'-bromo-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-one

生成物 1

HCID 58197813N-(5'-bromo-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-ylidene)cyanamide

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5′-bromo-5,6,8,9-tetrahydro-3′H-spiro[benzo[7]annulene-7,2′-benzofuran]-3′-one (0.1660 g, 0.48 mmol) in CH2Cl2 (5 mL) was added TiCl4 (1.0 M in CH2Cl2, 1.0 mL, 1.0 mmol) dropwise at room temperature. The reaction mixture was turned into orange precipitates in a few minutes. After 1 h, 1,3-bis(trimethylsilyl)carbodiimide (0.30 mL, 1.32 mmol) was added via a syringe. The precipitates were disappeared and the reaction mixture was turned into a red solution. The mixture was stirred at room temperature for 15 h and then quenched with ice, extracted with CH2Cl2, dried over Na2SO4. After the solvent was removed under reduced pressure, the crude product was directly used in the next step without further purification. LC-MS tR=2.27 min in 3 min chromatography, m/z 367, 369 (MH+).

後処理

  1. custominto orange precipitates in a few minutes
  2. customquenched with ice
  3. extractionextracted with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. customAfter the solvent was removed under reduced pressure
  6. customthe crude product was directly used in the next step without further purification
  7. waitLC-MS tR=2.27 min in 3 min chromatography, m/z 367, 369 (MH+)

出典と根拠

ORDレコード
ord-aee747c7ff3d4fd0a8164adbb7df7438
出典データセット
uspto-grants-2014_01
特許番号
US08633212B2

反応ノート

読み込み中…