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Tetrahydrofuran → 4,5,6-Trichloro-1-(2-methoxy-ethoxymethyl)-1H-benzoimidazole

HRID 1521434
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HRID 1521434 반응식
[Cl:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[C:4]([Cl:11])[C:3]=1[Cl:12].C1COCC1.CCN(C(C)C)C(C)C.Cl[CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33]>CCOC(C)=O>[Cl:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33])[C:6]=2[CH:5]=[C:4]([Cl:11])[C:3]=1[Cl:12]
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참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 3445854,5,6-trichloro-1H-benzoimidazole

생성물 1

HCID 669373514,5,6-Trichloro-1-(2-methoxy-ethoxymethyl)-1H-benzoimidazole

시약·촉매·용매 1

HCID 8857Ethyl Acetate
용매

실험 절차

To a mixture of 4,5,6-trichloro-1H-benzoimidazole (0.098 g, 0.446 mmol) and THF (2.5 mL) was added DIPEA (0.155 mL, 0.892 mmol), followed by 1-chloromethoxy-2-methoxy-ethane (0.057 ml, 0.49 mmol) at 23° C. After stirring for 18 h, EtOAc was added. The organic layer was washed with saturated aqueous NaHCO3. The aqueous layer was further extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified (FCC) to yield the titled compound as a mixture of regioisomers (0.084 g, 61%). MS (ESI/CI): mass calcd. for C11H11Cl3N2O2, 308.0; m/z found, 309.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 8.59 (s, 1H), 8.58 (s, 1H), 8.09 (s, 1H), 8.04 (d, J=8.5 Hz, 1H), 5.84 (s, 2H), 5.71 (s, 2H), 3.59-3.57 (m, 2H), 3.56-3.53 (m, 2H), 3.42-3.38 (m, 4H), 3.18 (s, 3H), 3.17 (s, 3H).

후처리

  1. washThe organic layer was washed with saturated aqueous NaHCO3
  2. extractionThe aqueous layer was further extracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified (FCC)

출처 및 근거

ORD 기록
ord-25c62d11adea4e0789f524f34cf887ed
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09073923B2

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