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

HRID 2259185

반응식

HRID 2259185 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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. 1H NMR (CDCl3, 200 MHz.) δ: 8.51(s,1H), 6.66(d,1H), 6.54(d,1H), 4.82(bs,1H), 3.97(s,3H), 3.82(s,3H), 1.24(s, 9H).

후처리

  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

출처 및 근거

ORD 기록
ord-9fd3c49acc3949dbaeffb920eeba00e0
출처 데이터셋
uspto-grants-1995_12
특허 번호
US05472933

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