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

HRID 2171251ノート

反応式

HRID 2171251 の反応式
S(Cl)([Cl:3])=O.[N+:5]([C:8]1[CH:9]=[C:10]([N:15]2[N:19]=[CH:18][CH:17]=[N:16]2)[C:11](O)=[N:12][CH:13]=1)([O-:7])=[O:6].[N+:20]([C:23]1[CH:24]=[C:25]([N:30]2[CH:34]=[CH:33][N:32]=[N:31]2)[C:26](O)=[N:27][CH:28]=1)([O-:22])=[O:21]>CN(C=O)C>[Cl:3][C:11]1[C:10]([N:15]2[N:19]=[CH:18][CH:17]=[N:16]2)=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:13][N:12]=1.[Cl:3][C:26]1[C:25]([N:30]2[CH:34]=[CH:33][N:32]=[N:31]2)=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[CH:28][N:27]=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

実験手順

Thionyl chloride (19 ml) and DMF (4 ml) were added to a mixture (5.32 g) of 5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridin-2-ol and 5-nitro-3-(1H-1,2,3-triazol-1-yl)pyridin-2-ol, followed by reflux for 1 hour. The reaction solution was poured into ice water, followed by extraction with ethyl acetate. The organic layers were washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure and the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 10:1). A light yellow solid of 2-chloro-5-nitro-3-(2H-1,2,3-triazol-2-yl)pyridine (0.72 g) and a yellow solid of 2-chloro-5-nitro-3-(1H-1,2,3-triazol-1-yl)pyridine (0.63 g) were thus obtained.

後処理

  1. temperatureby reflux for 1 hour
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layers were washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled away under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 10:1)

出典と根拠

ORDレコード
ord-3f6ad1a492144bd88f5bebe4154dc65b
出典データセット
uspto-grants-2015_06
特許番号
US09051310B2

反応ノート

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