Ammonium Chloride → 3-Amino-4-(4-hydroxy-phenylsulfanyl)-benzoic acid methyl ester

HRID 605349ノート

反応式

HRID 605349 の反応式
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[C:6]([N+:18]([O-])=O)[CH:5]=1.[NH4+].[Cl-]>CCO.CCOC(C)=O.[Fe]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[C:6]([NH2:18])[CH:5]=1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 668084784-(4-Hydroxy-phenylsulfanyl)-3-nitro-benzoic acid methyl ester

生成物 1

HCID 668086283-Amino-4-(4-hydroxy-phenylsulfanyl)-benzoic acid methyl ester

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A suspension of 4-(4-hydroxy-phenylsulfanyl)-3-nitro-benzoic acid methyl ester (5.60 g, 18 mmol), Fe powder (5.34 g, 92 mmol) and NH4Cl (4.91 g, 92 mmol) in aqueous EtOH [prepared from EtOH (50 mL) and H2O (50 mL)] was gradually heated to reflux and refluxed for 45 minutes. The reaction mixture was diluted with AcOEt (50 mL) and filtered through celite pad. The filtrate was evaporated and the aqueous residue was portioned between AcOEt and 10% NaHCO3. The organic layer was separated, washed with H2O and brine, dried over MgSO4 and evaporated to give pale yellow solid. The resulting solid was washed with i-Pr2O and dried at 40° C. for 3 days under reduced pressure to give the title compound as slightly yellow crystal (4.50 g, 90% by 2 steps).

後処理

  1. temperaturewas gradually heated
  2. temperatureto reflux
  3. temperaturerefluxed for 45 minutes
  4. filtrationfiltered through celite pad
  5. customThe filtrate was evaporated
  6. customThe organic layer was separated
  7. washwashed with H2O and brine
  8. dry with materialdried over MgSO4
  9. customevaporated
  10. customto give pale yellow solid
  11. washThe resulting solid was washed with i-Pr2O
  12. customdried at 40° C. for 3 days under reduced pressure

出典と根拠

ORDレコード
ord-5cea0750b472475c83da2014d7820e62
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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