O-methylhydroxylammonium chloride → 5,7-dihydro-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one O-methyl oxime

HRID 703170노트

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HRID 703170 반응식
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH2:10][S:11][C:12]2[NH:16][C:15]3[CH:17]=[C:18]4[C:22](=[CH:23][C:14]=3[N:13]=2)[C:21]([CH3:25])([CH3:24])[C:20](=O)[C:19]4([CH3:28])[CH3:27])[C:4]=1[CH3:29].[CH3:30][O:31][NH3+:32].[Cl-]>CO>[CH3:30][O:31][N:32]=[C:20]1[C:21]([CH3:25])([CH3:24])[C:22]2[C:18](=[CH:17][C:15]3[N:16]=[C:12]([S:11][CH2:10][C:5]4[C:4]([CH3:29])=[C:3]([O:2][CH3:1])[C:8]([CH3:9])=[CH:7][N:6]=4)[NH:13][C:14]=3[CH:23]=2)[C:19]1([CH3:28])[CH3:27]

참가 물질

4

반응물 2

HCID 11639O-methylhydroxylammonium chlorideHCID 221514375,7-dihydro-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)-methyl]thio]-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one

생성물 1

HCID 867411915,7-dihydro-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one O-methyl oxime

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

5 g of 5,7-dihydro-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethyli ndeno[5,6-d]imidazol-6(lH)-one and 40 g of 0-methylhydroxylamine hydrochloride in 250 ml of methanol were boiled at reflux for 16 hours under argon. After removing the solvent in vacuo the residue was partitioned between methylene chloride and water and the aqueous phase was extracted three times with methylene chloride. The combined organic extracts were made neutral with saturated sodium bicarbonate solution in the presence of ice and under argon gasification. After repeated extraction with methylene chloride the organic phases were dried over sodium sulfate and evaporated in vacuo. A red impurity was removed by chromatography on silica gel with ethyl acetate. The separation of the reaction product from starting material was carried out on silica gel using toluene/methyl isobutyl ketone/pyridine (80:18:2) as the elution agent. The purity of the fractions was assayed by thin-layer chromatography using the system ethyl acetate/ methyl isobutyl ketone/pyridine (80:18:2). By crystallization from acetone/water there was obtained 5,7-dihydro-2-[[(4- methoxy-3,5-dimethyl -2-pyridyl)methyl]thio]-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(lH)-one O-methyl oxime of melting point 110-112° .

후처리

  1. temperatureat reflux for 16 hours under argon
  2. customAfter removing the solvent in vacuo the residue
  3. customwas partitioned between methylene chloride and water
  4. extractionthe aqueous phase was extracted three times with methylene chloride
  5. extractionextraction with methylene chloride the organic phases
  6. dry with materialwere dried over sodium sulfate
  7. customevaporated in vacuo
  8. customA red impurity was removed by chromatography on silica gel with ethyl acetate
  9. customThe separation of the reaction product
  10. customBy crystallization from acetone/water there

출처 및 근거

ORD 기록
ord-c5a05ed1fa0242c38ac8192d8f64a8b4
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04981861

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