1-CHLORO-3,3,3-TRIFLUOROACETONE → HCID 22677441, compound

HRID 1837452Notes

Reaction equation

HRID 1837452 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10](=[S:12])[NH2:11])[CH:3]=1.Cl[CH2:14][C:15]([C:17]([F:20])([F:19])[F:18])=O>C(O)(=O)C>[Cl:9][C:6]1[C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=[C:4]([C:10]2[S:12][C:15]([C:17]([F:20])([F:19])[F:18])=[CH:14][N:11]=2)[N:5]=1

Participants

4

Reactant 2

HCID 27738371-CHLORO-3,3,3-TRIFLUOROACETONEHCID 22677254HCID 22677254, compound

Product 1

HCID 22677441HCID 22677441, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4, 5, 6-trichloropyridine-2-carbothioamide (2.85 g, 11.8 mmol) and 1-chloro-3,3,3-trifluoroacetone (2.59 g, 17.7 mmol) in glacial acetic acid (25 mL) was heated at reflux for 4 hours. Upon cooling, the solids formed were filtered and washed with water (3×100 mL) and sodium bicarbonate (3×50 mL). The solids were then dissolved in dichloromethane and the organic phase was washed with brine (150 mL), and dried (MgSO4). The solvent was removed and the residue purified by preparative liquid chromatography (90% acetonitrile in water) to give 2,3,4-trichloro-6-[5-(trifluoromethyl)-1,3-thiazol-2-yl]pyridine (0.70 g, 2.1 mmol); 1H NMR (CDCl3) δ 7.91 (s, 1H); 8.29 (s, 1H) and give 2,3,4-trichloro-6-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridine (0.20 g, 0.6 mmol); 1H NMR (CDCl3) δ 8.24 (1H, s), 8.39 (1H, s).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureUpon cooling
  4. customthe solids formed
  5. filtrationwere filtered
  6. washwashed with water (3×100 mL) and sodium bicarbonate (3×50 mL)
  7. dissolutionThe solids were then dissolved in dichloromethane
  8. washthe organic phase was washed with brine (150 mL)
  9. dry with materialdried (MgSO4)
  10. customThe solvent was removed
  11. customthe residue purified by preparative liquid chromatography (90% acetonitrile in water)

Sources & evidence

ORD record
ord-dc186100f1ff4602989b2875b1a1b032
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

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