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

HRID 2096514노트

반응식

HRID 2096514 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-775ce787c82842a4bd05cfdf2521fa53
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450308B2

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