4-Aminothiophenol → HCID 57469926、化合物

HRID 607332ノート

反応式

HRID 607332 の反応式
[Cl:1][C:2]1[S:3][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12](Cl)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)=[CH:5][N:6]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1>C(O)C>[Cl:1][C:2]1[S:3][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:26][C:23]3[CH:24]=[CH:25][C:20]([NH2:19])=[CH:21][CH:22]=3)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)=[CH:5][N:6]=1

参加物

4

反応物 2

HCID 145104-AminothiophenolHCID 60204766HCID 60204766、化合物

生成物 1

HCID 57469926HCID 57469926、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2-Chloro-5-(4-chloro-3-nitro-phenoxymethyl)-thiazole (from Example 25A) was reacted with 4-aminothiophenol in anhydrous ethanol and at reflux under a nitrogen atmosphere. The reaction was cooled to room temperature and the ethanol removed by rotary evaporation. The residue was taken up in water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Trituration of the solid with 4% ethyl acetate/methylene chloride afforded 4-(4-((2-chlorothiazol-5-yl)methoxy)-2-nitrophenylthio)aniline. A mixture of 4-(4-((2-chlorothiazol-5-yl)methoxy)-2-nitrophenylthio)aniline and di-tert-butyl dicarbonate in 1,4-dioxane was heated at reflux under a nitrogen atmosphere, and then additional Boc anhydride was added and the reaction allowed to reflux. The reaction was cooled to room temperature and the solvent removed by rotary evaporation in vacuo. The resulting solid was triturated with 2.5% ethyl acetate/methylene chloride to obtain tert-butyl 4-(4-((2-chlorothiazol-5-yl)methoxy)-2-nitrophenylthio)phenylcarbamate. A suspension of 4-(4-((2-chlorothiazol-5-yl)methoxy)-2-nitrophenylthio)phenylcarbamate, iron powder, and ammonium chloride in water and ethanol was heated. The reaction was cooled to room temperature. The mixture was diluted with ethyl acetate and washed with water and brine. The organic phase was dried, filtered, and concentrated under vacuum to provide the title compound.

後処理

  1. temperatureat reflux under a nitrogen atmosphere
  2. customthe ethanol removed by rotary evaporation
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0387252b51e742e192446d7115899d60
出典データセット
uspto-grants-2011_03
特許番号
US07915411B2

反応ノート

読み込み中…