1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine → HCID 11519366、化合物

HRID 433279ノート

反応式

HRID 433279 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 11519366HCID 11519366、化合物収率 49%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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) δ1.47 (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) δ14.66, 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).

後処理

  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)

出典と根拠

ORDレコード
ord-2c086bb0eb9b4bfdaf16e202f60e16d9
出典データセット
uspto-grants-2003_12
特許番号
US06667316B1

反応ノート

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