Sodium hydride → 2-Hydroxymethyl-3-methyl-4-{4-[2-(2-methyl-5-nitroimidazol-1-yl)ethylthio]butylthio}pyridine

HRID 342639

反応式

HRID 342639 の反応式
[H-].[Na+].[OH:3][CH2:4][C:5]1[C:10]([CH3:11])=[C:9]([S:12][CH2:13][CH2:14][CH2:15][CH2:16][SH:17])[CH:8]=[CH:7][N:6]=1.Cl[CH2:19][CH2:20][N:21]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][N:23]=[C:22]1[CH3:29]>CN(C=O)C.C(O)(=O)C>[OH:3][CH2:4][C:5]1[C:10]([CH3:11])=[C:9]([S:12][CH2:13][CH2:14][CH2:15][CH2:16][S:17][CH2:19][CH2:20][N:21]2[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][N:23]=[C:22]2[CH3:29])[CH:8]=[CH:7][N:6]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 832101-(2-Chloroethyl)-2-methyl-5-nitroimidazoleHCID 540725972-Hydroxymethyl-4-(4-mercaptobutylthio)-3-methylpyridine

生成物 1

HCID 538997552-Hydroxymethyl-3-methyl-4-{4-[2-(2-methyl-5-nitroimidazol-1-yl)ethylthio]butylthio}pyridine

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

0.43 g (15 mmol) of sodium hydride are initially introduced in 25 ml of DMF with ice-cooling. 3.33 g (13.7 mmol) of 2-hydroxymethyl-4-(4-mercaptobutylthio)-3-methylpyridine are added. After the evolution of gas has ended, 2.62 g (13.7 mmol) of 1-(2-chloroethyl)-2-methyl-5-nitroimidazole in 10 ml of DMF are added dropwise. The mixture is stirred with ice- cooling for 1 h. It is then diluted with 200 ml of ice-water and neutralized with acetic acid. The mixture is extracted 3 times with dichloromethane. The combined organic phases are washed 4 times with water, dried over magnesium sulfate, filtered and concentrated. The crude product is chromatographed on silica gel using ethyl acetate/methanol/conc. ammonia=89/10/1. The title compound is obtained on concentrating as a yellow crystallizate which is washed by stirring with diethyl ether. M.p. 86°-87° C.; yield 4 g (75% of theory).

後処理

  1. temperaturecooling
  2. temperaturecooling for 1 h
  3. extractionThe mixture is extracted 3 times with dichloromethane
  4. washThe combined organic phases are washed 4 times with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is chromatographed on silica gel

出典と根拠

ORDレコード
ord-fbaddc87e686466f8ec22980291fa16b
出典データセット
uspto-grants-1999_01
特許番号
US05859030

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