Phosphorus pentachloride → N-(2-chlorophenyl)-5-(methylsulfonyl)picolinimidoyl chloride

HRID 509591Notes

Reaction equation

HRID 509591 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][N:11]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:22]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]([Cl:22])[C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 67958704N-(2-chlorophenyl)-5-(methylsulfonyl)picolinamide

Product 1

HCID 86709639N-(2-chlorophenyl)-5-(methylsulfonyl)picolinimidoyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-(2-chlorophenyl)-5-(methylsulfonyl)picolinamide 5 (1.26 g, 0.0040 mol) in anhydrous benzene (20 mL) was added to PCl5 (1.26 g, 6.0 mmol) and the mixture was heated to reflux overnight. The solvent was removed and the residue was further dried under high vacuum. Crude N-(2-chlorophenyl)-5-(methylsulfonyl)picolinimidoyl chloride 6 was obtained as a yellow solid (1.60 g). The N-(2-chlorophenyl)-5-(methylsulfonyl)picolinimidoyl chloride 6 was dissolved into anhydrous THF (30 mL) and the reaction was cooled down to 0° C. and hydrazine monohydrate (9.0 mL) was added. The reaction was kept at 0° C. for 10 min and warmed to ambient temperature in 0.5 h. The solvent was removed and the residue was purified by column chromatography (eluting with hexane and ethyl acetate 1:1) to give N′-(2-chlorophenyl)-5-(methylsulfonyl) picolinimidohydrazide 7 as a yellow solid. Yield: 1.22 g, 92.0%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed
  4. customthe residue was further dried under high vacuum

Sources & evidence

ORD record
ord-64e259cac3b6462ba9f65a1534ddad7f
Source dataset
uspto-grants-2015_08
Patent number
US09096587B2

Reaction notes

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