2-Chloro-5-nitropyridine → HCID 13061966, compound

HRID 1758328Notes

Reaction equation

HRID 1758328 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][SH:11])=[N:5][N:4]=[N:3]1.[N+:12]([C:15]1[CH:16]=[CH:17][C:18](Cl)=[N:19][CH:20]=1)([O-:14])=[O:13]>[OH-].[Na+].CC(C)=O>[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][CH2:10][S:11][C:18]2[CH:17]=[CH:16][C:15]([N+:12]([O-:14])=[O:13])=[CH:20][N:19]=2)=[N:5][N:4]=[N:3]1

Participants

5

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 20509856HCID 20509856, compound

Product 1

HCID 13061966HCID 13061966, compoundYield 44.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 14798Sodium HydroxideSolvent

Procedure

1-Methyl-5-(3-mercaptopropyl)thio-1,2,3,4-tetrazole (1.9 g) is dissolved in 1 N aqueous sodium hydroxide (30 ml), and thereto is added dropwise a solution of 5-nitro-2-chloropyridine (1.9 g) in acetone (20 ml) under ice-cooling. After the addition, the mixture is stirred at room temperature for 3 hours. Acetone is distilled off and water is added to the residue. The mixture is extracted with ether, and the ether solution is washed with diluted aqueous sodium hydroxide and saturated aqueous sodium chloride and dried over sodium sulfate. After ether is distilled off, the residue is purified by column chromatography (Kieselgel 60), followed by eluting with n-hexane-ether (4:1) to give 1-methyl-5-[3-(5-nitro-2-pyridyl)thiopropyl]thio-1,2,3,4-tetrazole (1.4 g), pale brown liquid, nD29 =1.6289.

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. distillationAcetone is distilled off
  4. additionwater is added to the residue
  5. extractionThe mixture is extracted with ether
  6. washthe ether solution is washed with diluted aqueous sodium hydroxide and saturated aqueous sodium chloride
  7. dry with materialdried over sodium sulfate
  8. distillationAfter ether is distilled off
  9. customthe residue is purified by column chromatography (Kieselgel 60)
  10. washby eluting with n-hexane-ether (4:1)

Sources & evidence

ORD record
ord-3ff25f55841d405fa8cbfff7216f0561
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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