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Water → ethyl 1-({5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-1H-pyrazole-4-carboxylate

HRID 1257417
ノート
印刷プレビュー

反応式

HRID 1257417 の反応式
[NH2:1]/[C:2](=[N:14]\[OH:15])/[CH2:3][N:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[N:5]1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](Cl)=O.O>N1C=CC=CC=1>[F:16][C:17]([F:27])([F:28])[C:18]1[CH:19]=[C:20]([C:21]2[O:15][N:14]=[C:2]([CH2:3][N:4]3[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[N:5]3)[N:1]=2)[CH:24]=[CH:25][CH:26]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 58127695ethyl 1-[(2Z)-2-amino-2-hydroxyiminoethyl]pyrazole-4-carboxylate

生成物 1

HCID 66939395ethyl 1-({5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-1H-pyrazole-4-carboxylate収率 22.4%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
115 °C

実験手順

A solution of the compound (2.2 g) obtained in Example 114a in pyridine (40 mL) was cooled in an ice bath and 3-(trifluoromethyl)benzoyl chloride (4.16 g) was added. The reaction mixture was heated to 110-120° C. overnight, cooled to room temperature, and poured into water. The mixture was extracted with ethyl acetate. The ethyl acetate layer was separated, washed successively with 1N aqueous hydrochloric acid solution, and saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-petroleum ether) to give the title compound (0.85 g) as a colorless solid.

後処理

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. washwashed successively with 1N aqueous hydrochloric acid solution, and saturated aqueous sodium hydrogen carbonate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-petroleum ether)

出典と根拠

ORDレコード
ord-6e47c27f1a0e4e3699b0f8edf3979550
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08461348B2

反応ノート

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