Dibutyltin oxide → HCID 178477920, compound

HRID 1837447Notes

Reaction equation

HRID 1837447 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]#[N:11])[CH:3]=1.[N:12]([Si](C)(C)C)=[N+:13]=[N-:14].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1.C([Sn](=O)CCCC)CCC>[Cl:9][C:6]1[C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=[C:4]([C:10]2[NH:14][N:13]=[N:12][N:11]=2)[N:5]=1

Participants

6

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378Azidotrimethylsilane2×HCID 22677348HCID 22677348, compound

Product 1

HCID 178477920HCID 178477920, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 61221Dibutyltin oxideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4,5,6-trichloropyridine-2-carbonitrile (4.77 g, 23.0 mmol), azidotrimethylsilane (6.1 mL, 46.0 mmol) and dibutyltin oxide (0.57 g, 2.3 mmol) in toluene (75 mL) was heated to 90° C. After 3 hours, the reaction mixture was heated to reflux. After 7 hours, azidotrimethylsilane (0.5 mL, 3.8 mmol) and dibutyltin oxide (100 mg, 0.4 mmol) were added to drive the reaction to completion. After a short time, the volatiles were removed, and then the residue was taken up in methanol (50 mL) and stirred briefly at 25° C. The volatiles were removed and the residue was partitioned between saturated aq. NaHCO3 (200 mL), ethyl acetate (200 mL) and diethyl ether (100 mL). The layers were carefully separated in order to retain the insoluble white material in the aqueous fraction. The aqueous fraction then was acidified to pH 2 with concentrated HCl while stirring vigorously. The white precipitate was collected, washed with water and dried to provide 2,3,4-trichloro-6-(1H-tetrazol-5-yl)pyridine (5.4 g, 21.6 mmol), mp 197-198° C.

Workup

  1. temperaturethe reaction mixture was heated to reflux
  2. waitAfter 7 hours
  3. customthe reaction to completion
  4. customAfter a short time, the volatiles were removed
  5. customThe volatiles were removed
  6. customthe residue was partitioned between saturated aq. NaHCO3 (200 mL), ethyl acetate (200 mL) and diethyl ether (100 mL)
  7. customThe layers were carefully separated in order
  8. stirringwhile stirring vigorously
  9. customThe white precipitate was collected
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-41d9d789d3eb4023b9427ed1f4aa5a16
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

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