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

HRID 605124ノート

反応式

HRID 605124 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-9b8bc476cbe341e29e723bbcc0abcce3
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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