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

HRID 1620095노트

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HRID 1620095 반응식
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

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

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온도
90 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-316fa4aba8ab4053bac2136dadbeccc6
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772320B2

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