Ethanol → 4-Amino-5-(4-hydroxy-phenylsulfanyl)-thiophene-2-carboxylic acid (3-bromo-phenyl)-amide

HRID 605314노트

반응식

HRID 605314 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[S:12][C:13]([S:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)=[C:14]([N+:16]([O-])=O)[CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl-].[NH4+].O.C(O)C>O1CCCC1.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[S:12][C:13]([S:19][C:20]3[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=3)=[C:14]([NH2:16])[CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 670409995-(4-Hydroxy-phenylsulfanyl)-4-nitro-thiophene-2-carboxylic acid (3-bromo-phenyl)-amide

생성물 1

HCID 670406504-Amino-5-(4-hydroxy-phenylsulfanyl)-thiophene-2-carboxylic acid (3-bromo-phenyl)-amide

시약·촉매·용매 2

HCID 23925Iron촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of the product from Example 351D (1 equiv), iron powder (5 equiv) and ammonium chloride (3 equiv) in a mixture of tetrahydrofuran, water and ethanol was heated to reflux for 3 hours. The mixture was cooled to room temperature, filtered through a pad of celite, which was washed with ethanol and the resultant filtrate concentrated under vacuum. The material was then dissolved in water and extracted with ethyl acetate, the organic layer dried and concentrated under vacuum to provide the title product.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. filtrationfiltered through a pad of celite, which
  4. washwas washed with ethanol
  5. concentrationthe resultant filtrate concentrated under vacuum
  6. dissolutionThe material was then dissolved in water
  7. extractionextracted with ethyl acetate
  8. customthe organic layer dried
  9. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-0361d5052b0649b5a41e21c17847411b
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910595B2

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