Sodium Hydroxide → 4-(2-{4-[Hydroxyaminomethyl]phenoxy}ethyl)phenyl methanesulfonate

HRID 1595524Notes

Reaction equation

HRID 1595524 reaction equation
C([BH3-])#N.[Na+].[CH3:5][S:6]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[N:26][OH:27])=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)(=[O:8])=[O:7].Cl.O1CCOCC1.[OH-].[Na+]>CO.O1CCCC1.CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.O>[CH3:5][S:6]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][NH:26][OH:27])=[CH:23][CH:24]=2)=[CH:12][CH:11]=1)(=[O:8])=[O:7]

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 204431481,4-Dioxane hydrochlorideHCID 867573774-{2-[4-(Hydroxyiminomethyl)phenoxy]ethyl}phenyl methanesulfonate

Product 1

HCID 217049544-(2-{4-[Hydroxyaminomethyl]phenoxy}ethyl)phenyl methanesulfonateYield 59.3%

Reagents, catalysts & solvents 4

HCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-CatalystHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

1.88 g (30 mmole) sodium cyanoborohydride was added to a solution of 2.0 g (6 mmole) 4-{2-[4-(hydroxyiminomethyl)phenoxy]ethyl}phenyl methanesulfonate in 90 ml methanol and 18 ml tetrahydrofuran. Gas evolution was observed. 5 mg methyl orange was added resulting in a yellow colour. 4 M hydrochloric acid:dioxane (2:1) was added dropwise until the color was dark red (pH 2-3). The reaction mixture was poured into water, basified with 2 M sodium hydroxide (pH 9). More water was added and the product was extracted with ethyl acetate, dried, filtered and evaporated. The yellow residue was purified by chromatography on silica gel using ethyl acetate as eluent to give 1.2 g colourless oil of 4-(2-{4-[hydroxyaminomethyl]phenoxy}ethyl)phenyl methanesulfonate.

Workup

  1. customresulting in a yellow colour
  2. extractionthe product was extracted with ethyl acetate
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe yellow residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8d541b7cb87540ea893f6b0fa55817a5
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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