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Trimethylsilyl cyanide → (4-Methoxy-3-triisopropylsilanyloxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

HRID 2079117
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HRID 2079117 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.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].C[Si]([C:43]#[N:44])(C)C.[CH3:45][O:46][C:47]1[CH:54]=[CH:53][C:50]([CH:51]=O)=[CH:49][C:48]=1[O:55][Si:56]([CH:63]([CH3:65])[CH3:64])([CH:60]([CH3:62])[CH3:61])[CH:57]([CH3:59])[CH3:58]>ClCCl>[CH3:45][O:46][C:47]1[CH:54]=[CH:53][C:50]([CH:51]([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:43]#[N:44])=[CH:49][C:48]=1[O:55][Si:56]([CH:57]([CH3:58])[CH3:59])([CH:63]([CH3:64])[CH3:65])[CH:60]([CH3:61])[CH3:62]
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 86617914HCID 86617914, 화합물

생성물 1

HCID 59516995(4-Methoxy-3-triisopropylsilanyloxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]acetonitrile

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

After adding 3.19 g of 4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamine, 10g of MS3A, 1.56 g of Yb(OTf)3 and 4.84 ml of trimethylsilyl cyanide to a solution of 5.6 g of 4-methoxy-3-triisopropylsilanyloxybenzaldehyde [CAS No. 179260-96-6] in 98 ml of dichloromethane under a nitrogen atmosphere, the mixture was stirred at room temperature for 12 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give a white solid (5.59 g).

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

출처 및 근거

ORD 기록
ord-16f86bb6c4e34d27b98178ee37b22051
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07928228B2

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