Lawesson's reagent → HCID 22677254, compound

HRID 1837451Notes

Reaction equation

HRID 1837451 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([NH2:12])=O)[CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:22]2)=CC=1>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10](=[S:22])[NH2:12])[CH:3]=1

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 22677262HCID 22677262, compound

Product 1

HCID 22677254HCID 22677254, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 4, 5, 6-trichloropyridine-2-carboxamide (10.4 g, 46 mmol) and 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's Reagent, 22.0 g, 54 mmol) in toluene (150 mL) was heated under reflux for two hours. The reaction mixture was cooled, diluted with water (250 mL) and extracted with ethyl acetate (2×150 mL). The organic phase was dried (Na2SO4) and concentrated. The residue was purified by column chromatography (20% ethyl acetate in hexanes) to give 4, 5, 6-trichloropyridine-2-carbothioamide (6.5 g, 27 mmol): mp 168-169° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for two hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate (2×150 mL)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2d38566295054cf8958bb45fa9fc6d49
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

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