Hydrochloric Acid → N-(2-hydroxy-5-trifluoromethylphenyl)-2-methylsulfanylbenzamide

HRID 923806ノート

反応式

HRID 923806 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[OH:12].[CH3:13][S:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](O)=[O:18].CCN=C=NCCCN(C)C.Cl>N1C=CC=CC=1>[OH:12][C:3]1[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=1[NH:1][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=1[S:14][CH3:13]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 194982-(Methylthio)benzoic acidHCID 1202462-Amino-4-(trifluoromethyl)phenol

生成物 1

HCID 67981373N-(2-hydroxy-5-trifluoromethylphenyl)-2-methylsulfanylbenzamide収率 17.9%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2-amino-4-trifluoromethylphenol (1.00 g), 2-methylsulfanylbenzoic acid (0.95 g), WSC (1.41 g), and pyridine (20 ml) was stirred with heating at 80° C. for 2.5 hours. Into the reaction mixture cooled to room temperature, 1 mol/l of hydrochloric acid was poured, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine, sequentially, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.33 g of N-(2-hydroxy-5-trifluoromethylphenyl)-2-methylsulfanyl-benzamide (Compound (1B)-515).

後処理

  1. temperatureInto the reaction mixture cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine
  4. dry with materialsequentially, dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-14fd5edd6a7d4f8192a0e905b50f96cd
出典データセット
uspto-grants-2016_03
特許番号
US09278983B2

反応ノート

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