Water → HCID 86604368, 화합물

HRID 1158287노트

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HRID 1158287 반응식
[CH3:1]N(C)C=O.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[NH:17][CH:18]=[CH:19][N:20]=2)=[CH:11][CH:10]=1)([O-:8])=[O:7].[H-].[Na+].O.[C:24]([O:27][CH2:28][CH3:29])(=O)C>>[CH3:1][C@@:28]1([CH2:29][N:20]2[CH:19]=[CH:18][N:17]=[C:16]2[S:15][C:12]2[CH:13]=[CH:14][C:9]([N+:6]([O-:8])=[O:7])=[CH:10][CH:11]=2)[CH2:24][O:27]1

참가 물질

6

반응물 5

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 150774982-[(4-Nitrophenyl)thio]-1H-imidazole

생성물 1

HCID 86604368HCID 86604368, 화합물수율 91%

실험 절차

To N,N-dimethylformamide (5 ml) solution of 2-(4-nitrophenylthio)imidazole (500 mg) was added sodium hydride (90 mg) at 0° C., then reaction mixture was stirred at a room temperature for 30 minutes. After being cooled again the reaction mixture to 0° C., 2-methyl-2-oxiranylmethyl(S)-4-nitrobenzenesulfonate (618 mg) was added and stirred at a room temperature for 3.5 hours. Water and ethyl acetate were added to the reaction mixture, the organic layer was taken by separation. The ethyl acetate layer was washed with water and an aqueous solution being saturated with sodium chloride, then dried over anhydrous sodium sulfate. The residue obtained by removal of the solvent by distillation was purified by use of a silica gel column chromatography (eluent: dichlormethane/ethyl acetate=17/3), there was obtained (R)-1-(2-methyl-2-oxiranylmethyl)-2-(4-nitrophenylthio)imidazole (604 mg, yield: 91%) as yellow oily product.

후처리

  1. customreaction mixture
  2. temperatureAfter being cooled again the reaction mixture to 0° C.
  3. stirringstirred at a room temperature for 3.5 hours
  4. customthe organic layer was taken by separation
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe residue obtained by removal of the solvent by distillation
  8. customwas purified by use of a silica gel column chromatography (eluent: dichlormethane/ethyl acetate=17/3)

출처 및 근거

ORD 기록
ord-3ffea78fc0b449aea8d70c3d8357c4eb
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807843B2

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