Hydrochloric Acid → 5-Methanesulfonyl-pyridine-2-carboxylic acid (2-chloro-4-trifluoromethoxy-phenyl)-amide

HRID 509600노트

반응식

HRID 509600 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[NH2:13].C[Al](C)C.[CH3:18][S:19]([C:22]1[CH:23]=[CH:24][C:25]([C:28](OC)=[O:29])=[N:26][CH:27]=1)(=[O:21])=[O:20].Cl>C1(C)C=CC=CC=1.ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:11])([F:12])[F:10])[CH:5]=[CH:4][C:3]=1[NH:13][C:28]([C:25]1[CH:24]=[CH:23][C:22]([S:19]([CH3:18])(=[O:21])=[O:20])=[CH:27][N:26]=1)=[O:29]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 27340842-Chloro-4-(trifluoromethoxy)anilineHCID 16682925TrimethylaluminumHCID 53429647Methyl 5-(methylsulfonyl)picolinate

생성물 1

HCID 867096405-Methanesulfonyl-pyridine-2-carboxylic acid (2-chloro-4-trifluoromethoxy-phenyl)-amide

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

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온도
85 °C

실험 절차

2-Chloro-4-trifluoromethoxy-phenylamine (2.0 g, 9.29 mmol) in toluene (50 mL) was added to trimethylaluminum (2.0 M 4.65 mL) then methyl 5-(methylsulfonyl)picolinate 6 (1.0 g, 4.65 mol) was added and the mixture was heated to 80-90° C. for 2 h. The reaction was cooled down and 1N HCl solution (10 mL) was added to be acidic. Dichloromethane (100 mL) was then added and the organic phase was further washed with water (100 mL) and dried over sodium sulfate. The solvent was removed and the residue was mixed with ether (50 mL) and stirred for 0.5 h. The solid was filtered and dried to give 5-methanesulfonyl-pyridine-2-carboxylic acid (2-chloro-4-trifluoromethoxy-phenyl)-amide 7 as a light yellow solid. Yield: 1.26 g, 65%.

후처리

  1. temperatureThe reaction was cooled down
  2. washthe organic phase was further washed with water (100 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed
  5. additionthe residue was mixed with ether (50 mL)
  6. filtrationThe solid was filtered
  7. customdried

출처 및 근거

ORD 기록
ord-675cde833926421d9058a65d12f4f376
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096587B2

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