Selenium Dioxide → HCID 25228498, compound

HRID 1920689Notes

Reaction equation

[Se](=O)=[O:2].[CH3:4][N:5]([CH3:20])[C:6](=[O:19])[S:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([CH3:18])=[N:15]2)=[CH:10][CH:9]=1>>[CH3:20][N:5]([CH3:4])[C:6](=[O:19])[S:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([CH:18]=[O:2])=[N:15]2)=[CH:10][CH:9]=1

Participants

Reactant 2

HCID 24007Selenium Dioxide

HCID 25228125HCID 25228125, compound

Product 1

HCID 25228498HCID 25228498, compoundYield 57.1%

Conditions

Temperature: 100 °C

Procedure

Referring now to FIG. 22, under a nitrogen atmosphere, selenium dioxide (67.3 mg, 0.606 mmol) was added to a solution of 17 (99.1 mg, 0.4027 mmol) in xylenes (3 mL). The mixture was heated to 100° C. for 3 h, then filtered hot through cotton, rinsing with chloroform. The product was adsorbed onto silica gel and purified by column chromatography (4:6 EtOAc/hexane) to afford 18 (60 mg, 0.230 mmol, 57%) as a white solid: 1H NMR (CDCl3) δ 10.21 (1H, s), 8.41 (1H, d, J=8.8 Hz), 8.33 (1H, d, J=8.4 Hz), 8.06 (1H, d, J=8.8 Hz), 7.91 (1H, d, J=8.8 Hz), 7.80 (1H, dd, J=1.6, 8.4 Hz) 3.17 (3H, s), 3.07 (3H, s); 13C NMR (CDCl3) δ 193.6, 165.8, 152.9, 147.7, 137.2, 136.8, 135.6, 132.21, 129.9, 127.9, 118.1, 37.0; FTIR (neat) 2922, 2876, 1705, 1661, 1366, 853, 758 cm−1; MS (ESI) m/z calculated for (C13H12N2O2S+H)+ 261, found 261; HRMS (ESI) m/z calculated for (C13H12N2O2S+H)+ 261.0692, found 261.0661.

Workup

filtrationfiltered hot through cotton
washrinsing with chloroform
custompurified by column chromatography (4:6 EtOAc/hexane)

Sources & evidence

ORD record: ord-f36f55833e254140b0add7da4903960c
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173620B2

Reaction notes

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