Iodine → 3,5-diethyl 4-iodo-1H-pyrazole-3,5-dicarboxylate

HRID 33274

반응식

HRID 33274 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8][N:7]=1)=[O:5])[CH3:2].[I:16]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[CH2:14]([O:13][C:11]([C:9]1[C:10]([I:16])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[NH:7][N:8]=1)=[O:12])[CH3:15]

참가 물질

5

반응물 3

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 142184diethyl 1H-pyrazole-3,5-dicarboxylate

생성물 1

HCID 117392303,5-diethyl 4-iodo-1H-pyrazole-3,5-dicarboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 10 g 1H-Pyrazole-3,5-dicarboxylic acid diethyl ester in 400 ml acetonitrile 13 g ammonium cerium(iv) nitrate (CAN) and 7.17 g iodine were added and the mixture was heated to reflux for 5 h. Then, after cooling to RT, 30 ml sat. sodium thiosulfate solution were added. The mixture was extracted with ethyl acetate (3×100 ml), the combined organic layers were washed with water and then dried over MgSO4, filtered and the solvents were removed under reduced pressure. The residue was filtered through a pad of silica gel eluting with heptane/ethyl acetate 1:1.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 h
  3. extractionThe mixture was extracted with ethyl acetate (3×100 ml)
  4. washthe combined organic layers were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. filtrationThe residue was filtered through a pad of silica gel eluting with heptane/ethyl acetate 1:1

출처 및 근거

ORD 기록
ord-0d5a393a7b0d42febfff4291922d7261
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429581B2

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