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

HRID 2171251노트

반응식

HRID 2171251 반응식
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

참가 물질

6

반응물 3

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

생성물 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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3f6ad1a492144bd88f5bebe4154dc65b
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051310B2

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