Sodium Chloride → 1-(3-Chloro-2-hydroxypropyl)-2-nitroimidazole

HRID 1488372

반응식

HRID 1488372 반응식
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:15]([C@@H:17]1[O:19][CH2:18]1)[Cl:16].[Cl-].[Na+]>C(O)C>[OH:19][CH:17]([CH2:15][Cl:16])[CH2:18][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2]

참가 물질

6

반응물 4

HCID 5234Sodium ChlorideHCID 107012-NitroimidazoleHCID 11430Potassium CarbonateHCID 2734062(-)-Epichlorohydrin

생성물 1

HCID 1145421-(3-Chloro-2-hydroxypropyl)-2-nitroimidazole

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To 1.15 gram of 2-nitroimidazole in 20 mL of absolute ethanol was added 100 mg of potassium carbonate and 1.0 gram (R)-epichlorohydrin. The reaction mixture was refluxed overnight. The cooled reaction mixture is added to 150 mL of saturated aqueous sodium chloride containing 5% sodium bicarbonate. The reaction mixture was extracted with ethyl acetate (3×10 mL ) and the organic extract was dried over anhydrous sodium sulfate, filtered and concentrated to give 1.87 gram of the R enantiomer of 1-(2-hydroxy-3-chloropropyl)-2-nitroimidazole. A similar reaction procedure starting with (S)-epichlorohydrin gives 1.45 gram of the S enantiomer.

후처리

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe cooled reaction mixture
  3. extractionThe reaction mixture was extracted with ethyl acetate (3×10 mL )
  4. extractionthe organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-70d9dbf6a93f435bb2a15065f1477dc3
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05674693

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