Hydroxyamine hydrochloride → N-hydroxy-2-[[4-hexyloxybenzenesulfonyl](isobutyl)amino]acetamide

HRID 264319Notes

Reaction equation

HRID 264319 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([N:17]([CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:18][C:19](OCC)=[O:20])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl.[NH2:29][OH:30].C[O-].[Na+].[Na]>CO>[OH:30][NH:29][C:19](=[O:20])[CH2:18][N:17]([S:14]([C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:9][CH:10]=1)(=[O:16])=[O:15])[CH2:24][CH:25]([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 10834775Ethyl 2-[[4-hexyloxybenzenesulfonyl](isobutyl)amino]acetateHCID 10942334Sodium Methoxide

Product 1

HCID 10738924N-hydroxy-2-[[4-hexyloxybenzenesulfonyl](isobutyl)amino]acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Ethyl 2-[[4-hexyloxybenzenesulfonyl](isobutyl)amino]acetate (1.22 g, 3.05 mmol) is dissolved in methanol (15 mL). To this solution is added hydroxylamine hydrochloride (0.43 g, 6.11 mmol), followed by the addition of sodium methoxide, freshly prepared from sodium (0.35 g, 15.3 mmol) dissolved in methanol (5 mL). The reaction is stirred for 36 hours 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 crystallized from hexnae/ethyl acetate and collected by filtration to give N-hydroxy-2-[[4-hexyloxybenzenesulfonyl](isobutyl)amino]acetamide, m.p. 108°-110° 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 crystallized from hexnae/ethyl acetate
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-0b55bed1ad31402aa6efa71dcdffe34c
Source dataset
uspto-grants-1997_07
Patent number
US05646167

Reaction notes

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