Sodium hydride → 3-(1-Methyl-2-butynyloxy)-5-(3,5-dimethylpiperidino)-1,2,4-thiadiazole

HRID 2222133ノート

反応式

HRID 2222133 の反応式
CS([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH:13]([CH3:15])[CH2:12][CH:11]([CH3:16])[CH2:10]2)[S:6][N:5]=1)=O.[CH3:17][CH:18]([OH:22])[C:19]#[C:20][CH3:21].[H-].[Na+]>CN(C)C=O.COC(C)(C)C>[CH3:17][CH:18]([O:22][C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH:13]([CH3:15])[CH2:12][CH:11]([CH3:16])[CH2:10]2)[S:6][N:5]=1)[C:19]#[C:20][CH3:21]

参加物

6

反応物 3

HCID 24758Sodium hydride2 回HCID 1413443-Pentyn-2-ol2 回HCID 692175163-Methylsulfinyl-5-(3,5-dimethylpiperidino)-1,2,4-thiadiazole

生成物 1

HCID 587921293-(1-Methyl-2-butynyloxy)-5-(3,5-dimethylpiperidino)-1,2,4-thiadiazole収率 96.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

In 3 ml of N,N-dimethylformamide were dissolved 287 mg of 3-methylsulfinyl-5-(3,5-dimethylpiperidino)-1,2,4-thiadiazole and 103 mg of 3-pentyn-2-ol, and 58 mg of sodium hydride (oil suspension; content: 60 weight %) was added under ice-cooling. The mixture was stirred for 15 minutes and at room temperature for 1.5 hour. Furthermore, 30 mg of sodium hydride (oil suspension; content: 60 weight %) and 100 mg of 3-pentyn-2-ol were added in the mixture, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with tert-butyl methyl ether, and extracted with tert-butyl methyl ether after the addition of water. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 297 mg of 3-(1-methyl-2-butynyloxy)-5-(3,5-dimethylpiperidino)-1,2,4-thiadiazole (hereinafter, referred to as the present compound (21)).

後処理

  1. additionwas added under ice-
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. extractionextracted with tert-butyl methyl ether
  5. additionafter the addition of water
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-b4269e750c6743138312e91d77d4eade
出典データセット
uspto-grants-2008_05
特許番号
US07371746B2

反応ノート

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