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m-Tolylisothiocyanate → N-(m-tolylcarbamothioyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetamide

HRID 62044
ノート
印刷プレビュー

反応式

HRID 62044 の反応式
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.C([Li])CCC.[N:32]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[CH:36]=1)=[C:33]=[S:34]>O1CCCC1>[C:37]1([CH3:41])[CH:38]=[CH:39][CH:40]=[C:35]([NH:32][C:33]([N:21]([C:18]2[CH:19]=[CH:20][C:15]([C:12]3[N:13]=[CH:14][N:10]([C:7]4[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:25])[F:26])=[CH:9][CH:8]=4)[N:11]=3)=[CH:16][CH:17]=2)[C:22](=[O:24])[CH3:23])=[S:34])[CH:36]=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 69304m-TolylisothiocyanateHCID 118675042N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetamideHCID 178418339Butyllithium

生成物 1

HCID 118675189N-(m-tolylcarbamothioyl)-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetamide収率 55%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

反応条件

温度
0 °C

実験手順

To N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetamide in tetrahydrofuran (1.1 mL) cooled to −78° C. was added n-butyllithium (2.5 M, 0.13 mL). The reaction was stirred for 1 hour. 1-Isothiocyanato-3-methylbenzene was added and the solution was slowly warmed to 0° C. over 1 hour. The mixture was quenched with aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was purified via radial chromatography using a 97:3 chloroform/methanol mixture as eluent providing the title compound as a tan solid (0.062 g, 55%).

後処理

  1. customThe mixture was quenched with aqueous ammonium chloride
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via radial chromatography

出典と根拠

ORDレコード
ord-a1c8ac62b26b460c9c80443c7658ff7d
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09445594B2

反応ノート

読み込み中…

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