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

HRID 1521576Notes

Reaction equation

HRID 1521576 reaction equation
[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

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 44480908HCID 44480908, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-2cac286383844eedb65fa7ebd8fe3a95
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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