4-(5-Isopropoxythien-2-ylmethyl)-phenylamine → 2-[4-(5-Isopropoxythien-2-ylmethyl)phenyl]amino-imidazoline

HRID 2121056노트

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HRID 2121056 반응식
[CH:1]([O:4][C:5]1[S:9][C:8]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].S(O)(O)(=O)=O.Cl[C:24]1[NH:25][CH2:26][CH2:27][N:28]=1>ClCCl>[CH:1]([O:4][C:5]1[S:9][C:8]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:24]3[NH:28][CH2:27][CH2:26][N:25]=3)=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 120943954-(5-Isopropoxythien-2-ylmethyl)-phenylamineHCID 125033982-Chloroimidazoline sulfate

생성물 1

HCID 120943942-[4-(5-Isopropoxythien-2-ylmethyl)phenyl]amino-imidazoline수율 90%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
80 °C

실험 절차

To a solution of 4-(5-isopropoxythien-2-ylmethyl)-phenylamine (131 mg, 0.53 mmol) in aceonitrile (8 ml) was added 2-chloro-2-imidazoline sulfate (121 mg, 0.59 mmol) at 20-25° C. under argon. The mixture was heated at 80° C. for 1.5 hours. The mixture was diluted with dichloromethane and washed with sodium hydroxide, water, dried (Na2SO4) and concentrated to dryness. Purification by preparative TLC, eluting with ethyl acetate/methyl alcohol/isopropylamine, gave 2-[4-(5-isopropoxythien-2-ylmethyl)phenyl]amino-imidazoline (150 mg, 90%) as a thick yellow oil; 1H NMR (300 Mhz, CDCl3 δ 7.13 (d, J=8.4 Hz, 2H), 6.93 (d, J=8.4 Hz, 2H), 6.37 (dt, J=3.7, 1.0 Hz, 1H), 6.02 (d, J=3.7 Hz, 1H), 4.28 (quintet, J=6.2 Hz, 1H), 3.93 (bs, 2H), 3.52 (5, 4H), 3.24-3.5 (broad, 2H), 1.32 (d, J=6.2 Hz, 6H), MS m/e (%): 316 (M+1, 100%).

후처리

  1. washwashed with 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-6ab266792916463fad9e4f5a33de5068
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06693200B2

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