Reaction equation
[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]Participants
Procedure
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.
Workup
- stirringthe mixture was stirred at room temperature for 17 hr
- customDioxane as the solvent was removed under the reduced pressure
- extractionthe residue was extracted with methylene chloride
- dry with materialThe extract was dried over anhydrous sodium sulfate
- filtrationwas then filtered
- concentrationThe filtrate was concentrated under the reduced pressure
- customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)
Sources & evidence
- ORD record
- ord-9a17dec25ac14d9ba04d3633c5090ee7
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07871982B2
Linked notes
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