5-(1-Phenyl-1,2,3,4-tetrazol-5-yl)valeric acid → HCID 13203396, compound

HRID 35263Notes

Reaction equation

HRID 35263 reaction equation
[C:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)=[N:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>S(Cl)(Cl)=O>[CH2:1]([N:7]([CH2:11][CH3:12])[C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[N:9][N:10]=1)[CH3:2]

Participants

3

Reactant 1

HCID 142300655-(1-Phenyl-1,2,3,4-tetrazol-5-yl)valeric acid

Product 1

HCID 13203396HCID 13203396, compoundYield 190.7%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

Thionyl chloride (10 ml) is added to 5-(1-phenyl-1,2,3,4-tetrazol-5-yl)valeric acid (1.8 g) and the mixture is refluxed for 1 hour. After excess thionyl chloride is distilled off under reduced pressure, dry benzene is added to the residue and the remaining small amount of thionyl chloride is removed as the benzene azeotrope. The resulting residue is dissolved in dry pyridine (50 ml) and thereto is added dropwise with stirring N,N-Diethylamine (1.5 g) under ice-cooling. The mixture is stirred at room temperature for 1 hour and benzene is added to the reaction mixture. The mixture is washed with diluted hydrochloric acid, aqueous saturated sodium bicarbonate solution and aqueous saturated sodium chloride solution and dried over sodium sulfate. After benzene is distilled off, the residue is subjected to column chromatography (Kieselgel 60 produced by Merck) by eluting the column with chloroform to give N,N-diethyl-5-(1-phenyl-1,2,3,4-tetrazol-5-yl)valeramide (2.1 g), colorless liquid, nD25 =1.5303.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. distillationAfter excess thionyl chloride is distilled off under reduced pressure, dry benzene
  3. additionis added to the residue
  4. customthe remaining small amount of thionyl chloride is removed as the benzene azeotrope
  5. dissolutionThe resulting residue is dissolved in dry pyridine (50 ml)
  6. additionis added dropwise with stirring N,N-Diethylamine (1.5 g) under ice-
  7. temperaturecooling
  8. additionbenzene is added to the reaction mixture
  9. washThe mixture is washed with diluted hydrochloric acid, aqueous saturated sodium bicarbonate solution and aqueous saturated sodium chloride solution
  10. dry with materialdried over sodium sulfate
  11. distillationAfter benzene is distilled off
  12. customthe residue is subjected to column chromatography (Kieselgel 60 produced by Merck)
  13. washby eluting the column with chloroform

Sources & evidence

ORD record
ord-384427fce0da4341bc7e10bd80656a1c
Source dataset
uspto-grants-1988_08
Patent number
US04766120

Reaction notes

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