Hydroxyamine hydrochloride → HCID 10691191, compound

HRID 742048Notes

Reaction equation

HRID 742048 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][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:13][C:14](OCC)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.[NH2:29][OH:30].C[O-].[Na+]>CO>[OH:30][NH:29][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][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10668285HCID 10668285, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 10691191HCID 10691191, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-[[4-methoxybenzenesulfonyl](4-methoxybenzyl)amino]acetate (0.90 g, 2.3 mmol) is dissolved in methanol (20 mL). To this solution is added hydroxylamine hydrochloride (0.80 g, 11.5 mmol), followed by the addition of sodium methoxide (5.2 mL of a 2.67M solution). 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 washed with brine, dried (Na2SO4), and the solvent is evaporated. The product is recrystallized from ether/ethyl acetate to give N-hydroxy-2-[[4-methoxybenzenesulfonyl]-(4-methoxybenzyl)amino]acetamide, m.p. 134°-135.5° 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. washthe combined organic layers are washed with brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent is evaporated
  6. customThe product is recrystallized from ether/ethyl acetate

Sources & evidence

ORD record
ord-6ca86c877d204edd979e640b47fd5562
Source dataset
uspto-grants-1996_09
Patent number
US05552419

Reaction notes

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