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

HRID 2171251
Notes
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Reaction equation

HRID 2171251 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 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

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3f6ad1a492144bd88f5bebe4154dc65b
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09051310B2

Reaction notes

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