Thionyl Chloride → 2-chloro-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridine

HRID 340488ノート

反応式

HRID 340488 の反応式
S(Cl)([Cl:3])=O.O[C:6]1[C:11]([N:12]2[N:16]=[CH:15][CH:14]=[N:13]2)=[CH:10][C:9]([N+:17]([O-:19])=[O:18])=[CH:8][N:7]=1.O[C:21]1[C:26]([N:27]2[CH:31]=[CH:30][N:29]=[N:28]2)=[CH:25][C:24]([N+:32]([O-:34])=[O:33])=[CH:23][N:22]=1>CN(C=O)C>[Cl:3][C:6]1[C:11]([N:12]2[N:16]=[CH:15][CH:14]=[N:13]2)=[CH:10][C:9]([N+:17]([O-:19])=[O:18])=[CH:8][N:7]=1.[Cl:3][C:21]1[C:26]([N:27]2[CH:31]=[CH:30][N:29]=[N:28]2)=[CH:25][C:24]([N+:32]([O-:34])=[O:33])=[CH:23][N:22]=1

参加物

6

反応物 3

HCID 24386Thionyl ChlorideHCID 1785268425-nitro-3-(1H-1,2,3-triazol-1-yl)pyridin-2-olHCID 178526843HCID 178526843、化合物

生成物 2

HCID 866838702-chloro-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridineHCID 866838712-chloro-5-nitro-3-(1H-1,2,3-triazol-1-yl)pyridine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

Thionyl chloride (3.9 ml) and DMF (0.39 ml) were added to a mixture of 2-hydroxy-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridine and 2-hydroxy-5-nitro-3-(1H-1,2,3-triazol-1-yl)pyridine (385 mg), followed by stirring at 90° C. for 2 hours. The reaction solution was adjusted to room temperature, slowly added to ice water, and stirred under ice cooling for 30 minutes, followed by extraction with ethyl acetate. Then, the resultant was washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=9:1 to 2:1), and a yellow solid of 2-chloro-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridine (177 mg) and a yellow solid of 2-chloro-5-nitro-3-(1H-1,2,3-triazol-1-yl)pyridine (83 mg) were thus obtained.

後処理

  1. customwas adjusted to room temperature
  2. stirringstirred under ice cooling for 30 minutes
  3. extractionfollowed by extraction with ethyl acetate
  4. washThen, the resultant was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=9:1 to 2:1)

出典と根拠

ORDレコード
ord-d9f4c3ccc9e442fe89855f97ca467ed0
出典データセット
uspto-grants-2014_11
特許番号
US08895585B2

反応ノート

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