Water → 3-Amino-N-(3-bromo-phenyl)-4-(3-hydroxy-phenylsulfanyl)-benzamide

HRID 605124노트

반응식

HRID 605124 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:27])[C:10]2[CH:15]=[CH:14][C:13]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=3)=[C:12]([N+:24]([O-])=O)[CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[Cl-].[NH4+].O1CCCC1.O>C(O)C.[Fe]>[NH2:24][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[S:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=1)[C:9]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[O:27]

참가 물질

7

반응물 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 67040801N-(3-Bromo-phenyl)-4-(3-hydroxy-phenylsulfanyl)-3-nitro-benzamide

생성물 1

HCID 670401443-Amino-N-(3-bromo-phenyl)-4-(3-hydroxy-phenylsulfanyl)-benzamide수율 101.8%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매2회

실험 절차

A solution of the product of Example 79A (0.43 g, 0.97 mmol), iron powder (0.28 g, 5.0 mmol) and ammonium chloride (0.08 g, 1.5 mmol) in an ethanol (18 mL), tetrahydrofuran (18 mL), and water (6 mL) solution was heated to reflux for 3 hours. The resultant mixture was diluted with ethanol (50 mL) and filtered through a pad of celite. The filtrate was concentrated under vacuum to a volume of 10 mL, the solution diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined extracts were dried over sodium sulfate, filtered and concentrated under vacuum to provide the title compound (0.41 g, 98%).

후처리

  1. temperatureto reflux for 3 hours
  2. filtrationfiltered through a pad of celite
  3. concentrationThe filtrate was concentrated under vacuum to a volume of 10 mL
  4. additionthe solution diluted with water (50 mL)
  5. extractionextracted with ethyl acetate (2×50 mL)
  6. dry with materialThe combined extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-9b8bc476cbe341e29e723bbcc0abcce3
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910595B2

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