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Azobisisobutyronitrile → Ethyl 4-(bromomethyl)-5-(4-chlorophenyl)-3-(4-sulfamoylphenyl)thiophene-2-carboxylate

HRID 1518694
ノート
印刷プレビュー

反応式

HRID 1518694 の反応式
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:9]([CH3:21])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:13][CH:12]=1)=[O:5])[CH3:2].C1C(=O)N([Br:36])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>ClC1C=CC=CC=1>[Br:36][CH2:21][C:9]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:15][CH:16]=2)=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:7][C:8]=1[C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=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 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 68285835Ethyl-5-(4-chlorophenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylate2 回

生成物 1

HCID 68285313Ethyl 4-(bromomethyl)-5-(4-chlorophenyl)-3-(4-sulfamoylphenyl)thiophene-2-carboxylate収率 59.32%

試薬・触媒・溶媒 1

HCID 7964
Chlorobenzene
溶媒

反応条件

温度
85 °C

実験手順

To a stirred solution of Ethyl 5-(4-chlorophenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylate (Compound 1b, 4.0 g, 9.17 mmol) in chlorobenzene (50 ml) were added NBS (1.77 g, 10.09 mmol) and AIBN (1.65 g, 10.09 mmol) at 25° C. The reaction mixture was then stirred at 85° C. for 4 hr. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to room temperature and was quenched in aqueous sodium chloride solution (50 ml). The mixture so obtained was then extracted with Ethyl acetate (2×50 ml). The organic layer was washed with brine (1×50 ml) and dried over sodium sulfate and concentrated under reduced pressure to obtain crude product (4.0 g). The crude product was then purified by column chromatography over silica gel (100-200 mesh) using 40% ethyl acetate in hexanes as an eluent to obtain the title compound (2.8 g, 59.32%).

後処理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customwas quenched in aqueous sodium chloride solution (50 ml)
  3. customThe mixture so obtained
  4. extractionwas then extracted with Ethyl acetate (2×50 ml)
  5. washThe organic layer was washed with brine (1×50 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto obtain crude product (4.0 g)
  9. customThe crude product was then purified by column chromatography over silica gel (100-200 mesh)

出典と根拠

ORDレコード
ord-393e630eb28f46b49cdb6c004e7890eb
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09072731B2

反応ノート

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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