Dimethyl Disulfide → 5-(methylthio)-1-(4-vinylphenyl)-1H-1,2,4-triazole

HRID 1504718ノート

反応式

HRID 1504718 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1)=[CH2:2].[Li]CCCC.[CH3:19][S:20]SC>C1COCC1>[CH3:19][S:20][C:13]1[N:9]([C:6]2[CH:5]=[CH:4][C:3]([CH:1]=[CH2:2])=[CH:8][CH:7]=2)[N:10]=[CH:11][N:12]=1

参加物

5

反応物 3

HCID 12232Dimethyl DisulfideHCID 585499641-(4-vinylphenyl)-1H-1,2,4-triazoleHCID 178418339Butyllithium

生成物 1

HCID 866752215-(methylthio)-1-(4-vinylphenyl)-1H-1,2,4-triazole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of 1-(4-vinyl-phenyl)-1H-[1,2,4]-triazole (1 g, 5.8 mmol) in 50 mL of THF, was added n-BuLi (0.41 g, 6.4 mmol) at −78° C. and stirred for 30 min. To this dimethyldisulfide in THF (0.6 g, 6.43 mmol) was added and the resultant reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was quenched with a saturated aqueous NH4Cl solution and extracted with EtOAc (3×25 mL). The combined EtOAc layer was washed with brine and dried over sodium sulphate and concentrated under reduced pressure. The crude compound was purified by flash chromatography (SiO2, 100-200 mesh, 40% EtOAc in Pet ether) to afford the title compound as an off white solid (0.6 g, 48%): mp 68-70° C.; 1H NMR (400 MHz, CDCl3) δ 7.96 (s, 1H), 7.05 (m, 4H), 6.75 (dd, J=16.4, 10.7 Hz, 1H), 5.81 (d, J=16.4 Hz, 1H), 5.35 (d, J=10.7 Hz, 1H), 2.73 (s, 3H); ESIMS m/z 218.09 ([M+H]+).

後処理

  1. customthe resultant reaction mixture
  2. stirringwas stirred at ambient temperature for 16 h
  3. customThe reaction mixture was quenched with a saturated aqueous NH4Cl solution
  4. extractionextracted with EtOAc (3×25 mL)
  5. washThe combined EtOAc layer was washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude compound was purified by flash chromatography (SiO2, 100-200 mesh, 40% EtOAc in Pet ether)

出典と根拠

ORDレコード
ord-1145e33230ba492d87b85e1d17376e34
出典データセット
uspto-grants-2015_12
特許番号
US09215870B2

反応ノート

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