2-Chloroimidazoline sulfate → 2-[4-(5-Methoxythien-2-ylmethyl)phenyl]amino-imidazoline

HRID 993404노트

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HRID 993404 반응식
[CH3:1][O:2][C:3]1[S:7][C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.S(O)(O)(=O)=O.Cl[C:22]1[NH:23][CH2:24][CH2:25][N:26]=1>C(#N)C.ClCCl>[CH3:1][O:2][C:3]1[S:7][C:6]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:22]3[NH:26][CH2:25][CH2:24][N:23]=3)=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

참가 물질

5

반응물 2

HCID 125033982-Chloroimidazoline sulfateHCID 218768664-(5-Methoxythien-2-ylmethyl)-phenylamine

생성물 1

HCID 218768232-[4-(5-Methoxythien-2-ylmethyl)phenyl]amino-imidazoline수율 70%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

To a solution of [4-(5-methoxythien-2-ylmethyl)-phenylamine (145 mg, 0.66 mmol) in acetonitrile (10 ml) was added 2-chloro-2-imidazoline sulfate (155 mg, 0.76 mmol) at 20-25° C. under nitrogen. The resulting suspension was heated at 80° C. for 1.5 hours. The mixture was diluted with dichloromethane and washed with 10% sodium hydroxide, water, dried (Na2SO4), and concentrated to dryness. Purification by preparative TLC, eluting with ethyl acetate/methyl alcohol/isopropylamine, gave 2-[4-(5-methoxythien-2-ylmethyl)phenyl]amino-imidazoline (132 mg, 70%) as a yellow oil; 1H NMR (300 MHz, CDCl3) δ 7.12 (d, J=8.4 Hz, 2H), 6.93 (d, J=8.4 Hz, 2H), 6.39 (dt, J=3.7, 1.1 Hz, 1H), 5.98 (d, J=3.7 Hz, 1H), 3.92 (bs, 2H), 3.82 (S, 3H), 3.52 (S , 4H), 3.15-3.35 (broad, 2H).

후처리

  1. washwashed with 10% sodium hydroxide, water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated to dryness
  4. customPurification by preparative TLC
  5. washeluting with ethyl acetate/methyl alcohol/isopropylamine

출처 및 근거

ORD 기록
ord-e7e46d235c2c46faa77cf8d430e6f838
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06472536B1

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