Octopamine → 4-(1-Hydroxy-2-(2-nitrophenylsulfonamido)ethyl)phenyl 2-nitrobenzenesulfonate

HRID 253008

반응식

HRID 253008 반응식
[OH-:1].[Na+].[NH2:3][CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[OH:6].[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24])([O-:16])=[O:15]>O1CCOCC1>[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([O:13][C:10]1[CH:11]=[CH:12][C:7]([CH:5]([OH:6])[CH2:4][NH:3][S:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N+:14]([O-:16])=[O:15])(=[O:24])=[O:1])=[CH:8][CH:9]=1)(=[O:25])=[O:24])([O-:16])=[O:15]

참가 물질

5

반응물 3

HCID 4581OctopamineHCID 14798Sodium HydroxideHCID 155402-Nitrobenzenesulfonyl chloride

생성물 1

HCID 866312114-(1-Hydroxy-2-(2-nitrophenylsulfonamido)ethyl)phenyl 2-nitrobenzenesulfonate수율 97%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A 1 N aqueous solution of sodium hydroxide (79.1 ml, 79.1 mmol) solution was added to a solution of 5 g (26.4 mmol) of 4-(2-amino-1-hydroxyethyl)phenol in dioxane (50 ml), and the mixture was stirred at room temperature for 5 min. 2-Nitrobenzenesulfonyl chloride (14.6 g, 65.9 mmol) was added to this solution, and the mixture was stirred at room temperature for 17 hr. Dioxane as the solvent was removed under the reduced pressure, and the residue was extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate and was then filtered. The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to give 13.3 g (yield 97%) of the title compound.

후처리

  1. stirringthe mixture was stirred at room temperature for 17 hr
  2. customDioxane as the solvent was removed under the reduced pressure
  3. extractionthe residue was extracted with methylene chloride
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. filtrationwas then filtered
  6. concentrationThe filtrate was concentrated under the reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-9a17dec25ac14d9ba04d3633c5090ee7
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07871982B2

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