Water → HCID 86604368、化合物

HRID 1092870ノート

反応式

HRID 1092870 の反応式
[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

参加物

6

反応物 5

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

生成物 1

HCID 86604368HCID 86604368、化合物収率 91%

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c87ae22865f14714805eb6542287c51e
出典データセット
uspto-grants-2012_03
特許番号
US08129544B2

反応ノート

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