5,5'-((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))-bis(oxy))bis(4-(2-methoxyethoxy)-2-nitrobenzonitrile) → 5,5'-((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(2-amino-4-(2-methoxyethoxy)benzonitrile)

HRID 1405965노트

반응식

HRID 1405965 반응식
[O:1]([CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][C:30]1[C:31]([O:41][CH2:42][CH2:43][O:44][CH3:45])=[CH:32][C:33]([N+:38]([O-])=O)=[C:34]([CH:37]=1)[C:35]#[N:36])[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1[C:9]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:10][C:11]([N+:16]([O-])=O)=[C:12]([CH:15]=1)[C:13]#[N:14]>CC(O)=O.CC(O)C.[Fe]>[O:1]([CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1[C:9]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:10][C:11]([NH2:16])=[C:12]([CH:15]=1)[C:13]#[N:14])[CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][C:30]1[C:31]([O:41][CH2:42][CH2:43][O:44][CH3:45])=[CH:32][C:33]([NH2:38])=[C:34]([CH:37]=1)[C:35]#[N:36]

참가 물질

5

반응물 1

HCID 867011935,5'-((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))-bis(oxy))bis(4-(2-methoxyethoxy)-2-nitrobenzonitrile)

생성물 1

HCID 867011925,5'-((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(2-amino-4-(2-methoxyethoxy)benzonitrile)수율 82.8%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 176Acetic Acid용매HCID 3776Isopropanol용매

실험 절차

To a solution of 5,5′-((((oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(4-(2-methoxyethoxy)-2-nitrobenzonitrile) (0.2 g) in AcOH (10 mL) and i-PrOH (10 mL) was added iron powder (0.5 g). The resulting mixture was heated to reflux for 1 h. After reaction finished, the mixture was cooled to room temperature, filtered, the precipitate washed with EA (10 mL). The combined washings and filtrate were concentrated under reduced pressure and purification by silica chromatography to give 0.15 g of 5,5′-((((oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(2-amino-4-(2-methoxyethoxy)benzonitrile). 1H-NMR (400 MHz, CDCl3): δ: 6.90 (s, 2H), 6.25 (s, 2H), 4.20-4.16 (br, 4H), 4.15-4.02 (m, 8H), 3.82-3.79 (m, 4H), 3.77-3.75 (m, 4H), 3.72-3.70 (m, 4H), 3.68-3.66 (m, 4H), 3.43 (s, 6H).

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 1 h
  3. customAfter reaction
  4. filtrationfiltered
  5. washthe precipitate washed with EA (10 mL)
  6. concentrationThe combined washings and filtrate were concentrated under reduced pressure and purification by silica chromatography

출처 및 근거

ORD 기록
ord-d9f497a922f644fe855f1670e2c953a4
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916572B2

반응 노트

불러오는 중…