1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine → HCID 11519366, 화합물

HRID 1661738노트

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HRID 1661738 반응식
[N+:1]([C:4]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]=1[C:16]([OH:18])=O)([O-:3])=[O:2].[CH2:19]([O:21][C:22]1[CH:23]=[C:24]([CH:30]([NH2:36])[CH2:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH3:20]>C1(C)C=CC=CC=1>[CH2:19]([O:21][C:22]1[CH:23]=[C:24]([CH:30]([N:36]2[C:16](=[O:18])[C:5]3[C:6](=[CH:10][CH:11]=[C:12]([N+:13]([O-:15])=[O:14])[C:4]=3[N+:1]([O-:3])=[O:2])[C:7]2=[O:9])[CH2:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH3:20]

참가 물질

4

반응물 2

HCID 112887921-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamineHCID 187583613,4-Dinitrobenzene-1,2-dicarboxylic acid

생성물 1

HCID 11519366HCID 11519366, 화합물수율 49%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 3,4-dinitrophthalic acid (4.63 g, 18.1 mmol) and 2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine (4.94 g, 18.1 g) in toluene (70 mL) was heated to reflux for 15 hours. The water was removed by a Dean-Stark trap. To the reaction mixture was added ethyl acetate (150 mL). The organic layer was extracted with water, sodium hydrogen carbonate (sat), brine (100 mL each), and dried over magnesium sulfate. The solvent was removed in vacuo to give a solid. The solid was recrystallized from ethanol (300 mL) to give 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4,5-dinitroisoindoline-1,3-dione as an orange solid (4.35 g, 49% yield): mp, 122.0-124.0° C.; 1H NMR (CDCl3) δ 1.47 (t, J=6.9 Hz, 3H, CH3), 2.93 (s, 3H, CH3), 3.65 (dd, J=3.9, 14.3 Hz, 1H, CHH), 3:86 (s, 3H, CH3), 4.10 (q, J=6.9 Hz, 2H, CH2), 4.56 (dd, J=11.4, 14.1 Hz, 1H, CHH), 5.90 (dd, J=3.9, 11.1 Hz, 1H, NCH), 6.84 (d, J=8.0 Hz, 1H, Ar), 7.07-7.11 (m, 2H, Ar), 8.16 (d, J=8.2 Hz, 1H, Ar), 8.60 (d, J=7.9 Hz, 1H, Ar); 13C NMR (CDCl3) δ 14.66, 41.66, 49.57, 53.38, 55.98, 64.61, 111.61, 112.42, 120.64, 123.93, 126.18, 127.85, 131.93, 136.74, 138.10, 142.45, 148.77, 150.17, 161.57, 163.47; Anal Calcd for C20H19N3O10S+0.1 ethyl acetate: C, 48.78; H, 3.97; N, 8.37. Found: C, 48.50; H, 3.77; N, 8.07. (HNMR showed the sample contained ˜10% eq of ethyl acetate).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 15 hours
  3. customThe water was removed by a Dean-Stark trap
  4. additionTo the reaction mixture was added ethyl acetate (150 mL)
  5. extractionThe organic layer was extracted with water, sodium hydrogen carbonate (sat), brine (100 mL each)
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed in vacuo
  8. customto give a solid
  9. customThe solid was recrystallized from ethanol (300 mL)

출처 및 근거

ORD 기록
ord-939659b503d6415eb9f8eede7241c446
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030343B2

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