Water → N-(1,1-Dimethylethyl)-2-[(methoxyimino)methyl]-1H-pyrrole-3-sulfonamide

HRID 821

Reaction equation

HRID 821 reaction equation
Cl.[CH3:2][O:3][NH2:4].C([O-])(=O)C.[Na+].[CH3:10][C:11]([NH:14][S:15]([C:18]1[CH:22]=[CH:21][N:20](C)[C:19]=1[CH:24]=O)(=[O:17])=[O:16])([CH3:13])[CH3:12].O>CO>[CH3:13][C:11]([NH:14][S:15]([C:18]1[CH:22]=[CH:21][NH:20][C:19]=1[CH:24]=[N:4][O:3][CH3:2])(=[O:17])=[O:16])([CH3:10])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 19693840N-(1,1-Dimethylethyl)-2-formyl-1-methyl-1H-pyrrole-3-sulfonamide

Product 1

HCID 136144806N-(1,1-Dimethylethyl)-2-[(methoxyimino)methyl]-1H-pyrrole-3-sulfonamideYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3.91 g (46.8 mmol) of methoxyamine hydrochloride in 60 mL of methanol was added 3.84 g (46.8 mmol) of sodium acetate. After stirring the white suspension for ca. 15 minutes 5.72 g (23 mmol) of N-(1,1-dimethylethyl)-2-formyl-1-methyl-1H-pyrrole-3-sulfonamide was added in one portion. The white suspension was heated at a gentle reflux overnight ca. 16 hours. The reaction mixture was cooled to room temperature and poured into 500 mL of water. The aqueous mixture was extracted with four 100 mL portions of methylene chloride. The combined extracts were washed with water, dried (MgSO4) and concentrated in vacuo yielding 5.74 g of the title compound as a white solid, m.p. 99°-101° C.

Workup

  1. additionwas added in one portion
  2. temperatureThe white suspension was heated at
  3. temperaturea gentle reflux overnight ca. 16 hours
  4. extractionThe aqueous mixture was extracted with four 100 mL portions of methylene chloride
  5. washThe combined extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b75f1f1033143b794c5a9db7bc6a994
Source dataset
uspto-grants-1998_03
Patent number
US05723410

Linked notes

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