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

HRID 1521576노트

반응식

HRID 1521576 반응식
[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

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 44480908HCID 44480908, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-2cac286383844eedb65fa7ebd8fe3a95
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073929B2

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