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Trimethylsilyl cyanide → (8-ethyl-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

HRID 1698672
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HRID 1698672 반응식
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[N:3]=1.[CH2:14]([C:16]1[C:25]2[O:24][CH2:23][O:22][CH2:21][C:20]=2[CH:19]=[C:18]([CH:26]=O)[CH:17]=1)[CH3:15].C[Si]([C:32]#[N:33])(C)C.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3]>ClCCl>[CH2:14]([C:16]1[C:25]2[O:24][CH2:23][O:22][CH2:21][C:20]=2[CH:19]=[C:18]([CH:26]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([C:4]3[N:3]=[C:2]([CH3:1])[O:6][N:5]=3)=[CH:8][CH:9]=2)[C:32]#[N:33])[CH:17]=1)[CH3:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 82115Trimethylsilyl cyanideHCID 2733225Ytterbium triflateHCID 181881764-(5-Methyl-1,2,4-oxadiazol-3-yl)anilineHCID 595172958-ethyl-4H-benzo[1,3]dioxine-6-carbaldehyde

생성물 1

HCID 67277334(8-ethyl-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

After adding 794 mg of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 871 mg of 8-ethyl-4H-benzo[1,3]dioxine-6-carbaldehyde, 1 g of MS3A and 1 ml of trimethylsilyl cyanide to a solution of 281 mg of Yb(OTf)3 in 20 ml of dichloromethane under a nitrogen atmosphere, the mixture was stirred at room temperature for 2 days. The reaction mixture was filtered through celite, and the celite was washed with 100 ml of ethyl acetate. The organic layer was concentrated under reduced pressure to give (8-ethyl-4H-benzo[1,3]dioxin-6-yl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile (crude product) as a light yellow solid.

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe celite was washed with 100 ml of ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6009bf3f40894c2bb9c7792bd889766a
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163787B2

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