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

HRID 509596노트

반응식

HRID 509596 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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, 0.0060 mol) 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 compound 6 was dissolved into anhydrous THF (30 mL) and the reaction was cooled down to 0° C. and hydrazine hydrate (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%.

후처리

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

출처 및 근거

ORD 기록
ord-445d20486157401781622a6306e127f2
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096587B2

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