Carbon Disulfide → HCID 86623878、化合物

HRID 1696645ノート

反応式

HRID 1696645 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[C:4]([F:10])[C:3]=1[NH2:11].[C:12](=S)=[S:13]>O1CCCC1>[F:10][C:4]1[C:3]2[NH:11][C:12](=[S:13])[NH:1][C:2]=2[CH:7]=[C:6]([F:8])[C:5]=1[F:9]

参加物

4

反応物 2

HCID 6348Carbon Disulfide4 回HCID 27739583,4,5-Trifluorobenzene-1,2-diamine

生成物 1

HCID 86623878HCID 86623878、化合物収率 22.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1,2-diamino-3,4,5-trifluoro-benzene (2.5 g, 15.4 mmol) in 20 mL of tetrahydrofuran under argon, are added 2.3 mL (38.6 mmol) of carbon disulfide. The reaction mixture is heated at reflux temperature for 3 h, upon which 2.3 mL (38.6 mmol) of carbon disulfide are added and reflux is maintained for 16 h. Carbon disulfide 2.3 mL (38.6 mmol) is added and reflux is maintained for 8 h, upon which 2.3 mL (38.6 mmol) of carbon disulfide are added and reflux is maintained for 16 h. The reaction mixture is then cooled to room temperature and concentrated to dryness under reduced pressure. The residue is purified by chromatography on a prepacked 90 g 15-40 μm silica gel cartridge (eluting solvent: cyclohexane/ethyl acetate 90/10 v/v; rate: 35 mL/min). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure. The residue is purified by chromatography on a prepacked 90 g 15-40 μm silica gel cartridge (eluting solvent: dichloromethane/methanol 100/0, then 98/2 v/v; rate: 40 mL/min). The fractions containing the desired product are combined and concentrated to dryness under reduced pressure. 0.72 g of 4,5,6-trifluoro-1,3-dihydro-benzimidazole-2-thione is obtained as an off-white solid. LCMS-DAD-ELSD: 203(−): [M−H]−; 205(+): [M+H]+.

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux temperature for 3 h
  3. temperaturereflux
  4. temperatureis maintained for 16 h
  5. temperaturereflux
  6. additionare added
  7. temperaturereflux
  8. temperatureis maintained for 16 h
  9. concentrationconcentrated to dryness under reduced pressure
  10. customThe residue is purified by chromatography on a prepacked 90 g 15-40 μm silica gel cartridge (eluting solvent: cyclohexane/ethyl acetate 90/10 v/v; rate: 35 mL/min)
  11. additionThe fractions containing the desired product
  12. concentrationconcentrated to dryness under reduced pressure
  13. customThe residue is purified by chromatography on a prepacked 90 g 15-40 μm silica gel cartridge (
  14. washeluting solvent
  15. additionThe fractions containing the desired product
  16. concentrationconcentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-61a4e794bf464920ba1256731f17664e
出典データセット
uspto-grants-2012_04
特許番号
US08163768B2

反応ノート

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