Hydrochloric Acid → N-(3-Bromo-phenyl)-4-(3-hydroxy-phenylsulfanyl)-3-nitro-benzamide

HRID 605123ノート

反応式

HRID 605123 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13](Cl)=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[OH:21][C:22]1[CH:23]=[C:24]([SH:28])[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13]([S:28][C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([OH:21])[CH:23]=3)=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 1368133N-(3-bromophenyl)-4-chloro-3-nitrobenzamideHCID 27366133-Hydroxybenzenethiol

生成物 1

HCID 67040801N-(3-Bromo-phenyl)-4-(3-hydroxy-phenylsulfanyl)-3-nitro-benzamide収率 97%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of N-(3-Bromo-phenyl)-4-chloro-3-nitro-benzamide (from Example 26A) (0.356 g, 1.0 mmol), 3-hydroxythiophenol (0.126 g, 1.0 mmol) and cesium carbonate (0.65 g, 2.0 mmol) in N,N-dimethylformamide (5 mL) was heated to 95° C. for 3 hours. After cooling to room temperature the mixture was poured into ice water (20 mL) and the resultant solution acidified with 1N aqueous hydrochloric acid. The solution was then extracted with ethyl acetate (3×10 mL), the combined extracts dried over magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (0.430 g, 97%).

後処理

  1. extractionThe solution was then extracted with ethyl acetate (3×10 mL)
  2. dry with materialthe combined extracts dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-8fdd92dbf8994060aeacb43754c9b929
出典データセット
uspto-grants-2011_03
特許番号
US07910595B2

反応ノート

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