Lawesson's reagent → 2H-1-Benzazepine-2-thione, 1,3,4,5-tetrahydro-7-(3-pyridinyl)-

HRID 1521576ノート

反応式

HRID 1521576 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[CH:9][C:10]3[NH:16][C:15](=O)[CH2:14][CH2:13][CH2:12][C:11]=3[CH:18]=2)[CH:2]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:28]2)=CC=1>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[CH:9][C:10]3[NH:16][C:15](=[S:28])[CH2:14][CH2:13][CH2:12][C:11]=3[CH:18]=2)[CH:2]=1

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 44480908HCID 44480908、化合物

生成物 1

HCID 899616802H-1-Benzazepine-2-thione, 1,3,4,5-tetrahydro-7-(3-pyridinyl)-

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

The title compound from Example 2 Step D (0.200 g, 0.839 mmol) and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane2,4-disulfide (0.255 g, 0.629 mmol) were suspended in toluene (1.7 mL) and then heated to reflux for several hours. The reaction solution was then cooled to room temperature and concentrated. Purification by flash chromatography on silica gel (0-10% methanol in ethyl acetate) provided the title compound: LCMS m/z 255.03 [M+H]+; 1H NMR (500 MHz, d6-DMSO) δ 8.81 (s, 1H), 8.48-8.47 (m, 1H), 8.02 (d, J=7.9 Hz, 1H), 7.58-7.56 (m, 2H), 7.42 (dd, J=4.8, 7.9 Hz, 1H), 7.13 (d, J=8.1 Hz, 1H), 2.74-2.71 (m, 2H), 2.68-2.65 (m, 2H), 2.26-2.20 (m, 2H).

後処理

  1. temperatureheated
  2. temperatureto reflux for several hours
  3. concentrationconcentrated
  4. customPurification by flash chromatography on silica gel (0-10% methanol in ethyl acetate)

出典と根拠

ORDレコード
ord-2cac286383844eedb65fa7ebd8fe3a95
出典データセット
uspto-grants-2015_07
特許番号
US09073929B2

反応ノート

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