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

HRID 2096514ノート

反応式

HRID 2096514 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-775ce787c82842a4bd05cfdf2521fa53
出典データセット
uspto-grants-2013_05
特許番号
US08450308B2

反応ノート

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