Triethylamine → HCID 178420719, compound

HRID 1247933Notes

Reaction equation

HRID 1247933 reaction equation
Cl.Cl[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[SH:9][C:10]1[NH:14][N:13]=[N:12][N:11]=1.C(N(CC)CC)C>CN(C)C=O>[NH:11]1[C:10]([S:9][C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)=[N:14][N:13]=[N:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 818524-Chloropyridine hydrochlorideHCID 178527994HCID 178527994, compound

Product 1

HCID 178420719HCID 178420719, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chloropyridine hydrochloride (7.25 g), 5-mercapto-1H-tetrazole (4.93 g) and triethylamine (14.64 g) in dimethylformamide (120 ml) was stirred for one hour at 82° to 85° C. and then cooled in an ice bath. The resulting precipitates were removed by filtration and the filtrate was mixed with water (60 ml). The aqueous solution was adjusted to pH 2 with 2N hydrochloric acid and evaporated to dryness under reduced pressure. The residue was triturated in chloroform (300 ml) and the resulting precipitates were collected by filtration and washed with the same solvent. To the precipitates was added ethanol (650 ml) and an insoluble material was removed by filtration. The filtrate was evaporated to dryness to give 4-(1H-tetrazol-5-ylthio)pyridine (4.03 g), mp. 159° to 161° C. (dec.).

Workup

  1. temperaturecooled in an ice bath
  2. customThe resulting precipitates
  3. customwere removed by filtration
  4. additionthe filtrate was mixed with water (60 ml)
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was triturated in chloroform (300 ml)
  7. customthe resulting precipitates
  8. filtrationwere collected by filtration
  9. washwashed with the same solvent
  10. additionTo the precipitates was added ethanol (650 ml)
  11. customan insoluble material was removed by filtration
  12. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-7308ee4e5c174ce58ef20bfe07f1936c
Source dataset
uspto-grants-1985_06
Patent number
US04521413

Reaction notes

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