Hydroxyamine hydrochloride → N-hydroxy-2-[[4-methoxybenzenesulfonyl](benzyl)amino]acetamide

HRID 2209696Notes

Reaction equation

HRID 2209696 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:13][C:14](OCC)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.[NH2:27][OH:28].C[O-].[Na+].[Na]>CO>[OH:28][NH:27][C:14](=[O:15])[CH2:13][N:12]([S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 3503631Ethyl 2-[[4-methoxybenzenesulfonyl](benzyl)amino]acetateHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 10594000N-hydroxy-2-[[4-methoxybenzenesulfonyl](benzyl)amino]acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Ethyl 2-[[4-methoxybenzenesulfonyl](benzyl)amino]acetate (11.20 g, 30.9 mmol) is dissolved in methanol (100 mL). To this solution is added hydroxylamine hydrochloride (4.31 g, 62.0 mmol), followed by the addition of sodium methoxide, freshly prepared from sodium (2.14 g, 93.0 mmol) dissolved in methanol (55 mL). The reaction is stirred overnight at room temperature. The reaction is worked up by partitioning between dilute hydrochloric acid (pH=~3) and ethyl acetate. The aqueous phase is extracted well with ethyl acetate, the combined organic layers are dried (Na2SO4), and the solvent is evaporated. The product is purified by silica gel chromatography (75% ethyl acetate/hexane) to give N-hydroxy-2-[[4-methoxybenzenesulfonyl](benzyl)amino]acetamide, m.p. 112°-114° C.

Workup

  1. customby partitioning between dilute hydrochloric acid (pH=~3) and ethyl acetate
  2. extractionThe aqueous phase is extracted well with ethyl acetate
  3. dry with materialthe combined organic layers are dried (Na2SO4)
  4. customthe solvent is evaporated
  5. customThe product is purified by silica gel chromatography (75% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-499543356daf4f1b9d6259f2dba9ff0d
Source dataset
uspto-grants-1995_10
Patent number
US05455258

Reaction notes

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