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

HRID 509600ノート

反応式

HRID 509600 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
85 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-675cde833926421d9058a65d12f4f376
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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