Carbon Disulfide → HCID 86623878, compound

HRID 1696645Notes

Reaction equation

HRID 1696645 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 86623878HCID 86623878, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-61a4e794bf464920ba1256731f17664e
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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