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

HRID 607222노트

반응식

HRID 607222 반응식
[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

참가 물질

8

반응물 3

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 668084784-(4-Hydroxy-phenylsulfanyl)-3-nitro-benzoic acid methyl ester

생성물 1

HCID 668086283-Amino-4-(4-hydroxy-phenylsulfanyl)-benzoic acid methyl ester수율 79%

시약·촉매·용매 4

HCID 23925Iron촉매HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-b639d4c3969040dd94deebb7615f6577
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915411B2

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