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

HRID 607222ノート

反応式

HRID 607222 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.CN(C=O)C.[Cl-].[NH4+]>O1CCCC1.O.C(O)C.[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

8

反応物 3

HCID 6228DimethylformamideHCID 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収率 79%

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A suspension of the product of Example 113A (as a mono DMF adduct)(7.25 g, 19.23 mmol) ammonium chloride (1.54 g, 28.8 mmol) and iron powder (5.37 g, 96.15 mmol) in tetrahydrofuran (75 mL), water (25 mL) and ethanol (75 mL) was heated at reflux for 3 hours. The reaction was cooled to room temperature, and the mixture was filtered through a pad of celite, which was then washed with methanol, and the filtrate concentrated to a solid under vacuum. The residue was then dissolved in water (100 mL) and extracted with dichloromethane (2×50 mL). The combined organic extracts were washed with brine (25 mL), dried over magnesium sulfate, filtered, and concentrated under vacuum to provide the title compound as a white solid (4.2 g, 79%).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. filtrationthe mixture was filtered through a pad of celite, which
  4. washwas then washed with methanol
  5. concentrationthe filtrate concentrated to a solid under vacuum
  6. dissolutionThe residue was then dissolved in water (100 mL)
  7. extractionextracted with dichloromethane (2×50 mL)
  8. washThe combined organic extracts were washed with brine (25 mL)
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-b639d4c3969040dd94deebb7615f6577
出典データセット
uspto-grants-2011_03
特許番号
US07915411B2

反応ノート

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