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

HRID 509591ノート

反応式

HRID 509591 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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%.

後処理

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

出典と根拠

ORDレコード
ord-64e259cac3b6462ba9f65a1534ddad7f
出典データセット
uspto-grants-2015_08
特許番号
US09096587B2

反応ノート

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