Ethanol → HCID 86595681、化合物

HRID 1241921ノート

反応式

HRID 1241921 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[C:3]=1[CH:4]=[N:5][OH:6].[Cl:17][CH:18]([Cl:30])[C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24](C#C)[CH:23]=1)=[O:20].[CH3:31][C:32]1[CH:37]=CC(S([N-]Cl)(=O)=O)=CC=1.O.[Na+].C([OH:47])C>CO>[Cl:30][CH:18]([Cl:17])[C:19]([NH:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=1[C:31]([C:32]1[O:6][N:5]=[C:4]([C:3]2[C:7]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[CH:8][CH:9]=[CH:10][C:2]=2[Cl:1])[CH:37]=1)=[O:47])=[O:20]

参加物

6

反応物 4

HCID 702EthanolHCID 2804962HCID 2804962、化合物HCID 16218604Benzenesulfonamide, N-chloro-4-methyl-, sodium salt, monohydrateHCID 136334122HCID 136334122、化合物

生成物 1

HCID 86595681HCID 86595681、化合物収率 13%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

2-Chloro-6-(4-pyridyl)benzaldoxime (85 mg, 0.37 mmol), 2,2-dichloro-N-(3-ethynylphenyl) acetamide (78 mg, 0.34 mmol), chloramine-T hydrate (100 mg, 0.44 mmol) and ethanol (2 mL) were combined in a microwave vial and sealed with a crimp seal. The mixture was microwaved at 100° C. for 600 seconds. The resulting mixture was concentrated under reduced pressure and taken up in ethyl acetate. This organic solution was washed with ice-cold 1N sodium hydroxide and brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel, eluting with 98:2 methylene chloride:methanol to provide compound number 684, 2,2-dichloro-N-[2-[3-(2-chloro-6-(4-pyridyl)phenyl)-5-isoxazoyl]phenyl]acetamide (20 mg, 13% yield) as a light yellow solid. NMR (300 MHz, CDCl3): 8.5 (m, 2H), 8.25 (broad s, 1H), 8.0 (m, 1H), 7.8 (m, 1H), 7.7–7.4 (m, 5H), 7.3 (m, 2H), 6.5 (s, 1H), 6.05 ppm (s, 1H).

後処理

  1. customsealed with a crimp
  2. customseal
  3. customThe mixture was microwaved at 100° C. for 600 seconds
  4. concentrationThe resulting mixture was concentrated under reduced pressure
  5. washThis organic solution was washed with ice-cold 1N sodium hydroxide and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by flash column chromatography on silica gel
  10. washeluting with 98:2 methylene chloride

出典と根拠

ORDレコード
ord-880f804080b5411f9a5f6d91014a27dd
出典データセット
uspto-grants-2006_10
特許番号
US07115642B2

反応ノート

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