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Sodium Sulfite → (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-[(methylsulfonyl)methyl]phenyl)acrylamide

HRID 30727
ノート
印刷プレビュー

反応式

HRID 30727 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25]SC)=[CH:21][CH:20]=2)=[O:17])=[CH:4][CH:3]=1.Cl[C:29]1C=CC=C(C(OO)=O)C=1.[S:39]([O-:42])([O-])=[O:40].[Na+].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]/[C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][S:39]([CH3:29])(=[O:42])=[O:40])=[CH:23][CH:24]=2)=[O:17])=[CH:6][CH:7]=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 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 69210621(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-{4-[(methylthio)methyl]phenyl}acrylamide

生成物 1

HCID 10047367(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-[(methylsulfonyl)methyl]phenyl)acrylamide収率 75%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
0 °C

実験手順

A mixture of (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-{4-[(methylthio)methyl]phenyl}acrylamide (600 mg), m-chloroperbenzoic acid (780 mg) and tetrahydrofuran (50 mL) was stirred at 0° C. for 20 min. A saturated aqueous sodium sulfite solution was added to the reaction mixture, and the mixture was further stirred for 10 min. and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate, and then with saturated brine, dried (MgSO4) and concentrated. The obtained solid was recrystallized from acetone-hexane to give (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]-N-(4-[(methylsulfonyl) methyl]phenyl)acrylamide (490 mg, yield 75%) as colorless prism crystals. melting point: 251-252° C.

後処理

  1. stirringthe mixture was further stirred for 10 min.
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialwith saturated brine, dried (MgSO4)
  5. concentrationconcentrated
  6. customThe obtained solid was recrystallized from acetone-hexane

出典と根拠

ORDレコード
ord-84d27d96890147c68d709c8dcc2a656c
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07423159B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート