Hydrazoic acid → HCID 12806312, compound

HRID 1758293Notes

Reaction equation

HRID 1758293 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])(=O)[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.N(Cl)Cl.[NH:21]=[N+:22]=[N-:23]>C1C=CC=CC=1>[CH3:2][C:1]1[N:4]([CH2:5][CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])[N:23]=[N:22][N:21]=1

Participants

6

Reactant 4

HCID 24530Hydrazoic acidHCID 24819Phosphorus pentachlorideHCID 76939ChlorimideHCID 12806311HCID 12806311, compound

Product 1

HCID 12806312HCID 12806312, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Methyl 4-acetamidobutyrate (8 g) is dissolved in benzene (80 ml). Phosphorus pentachloride (12 g, 0.055 mol) is added to the solution with stirring and ice-cooling. The mixture is stirring at room temperature for 1.5 hours and then concentrated to about 1/3 volume under reduced pressure. To the resulting iminochloride solution is added dropwise a solution of hydrogen azide in benzene (0.0173 mol/10 ml, 57.8 ml) with stirring and ice-cooling. The mixture is stirred at room temperature for 1 hour, allowed to stand for overnight and gently refluxed for 2 hours. The reaction mixture is concentrated and ice-water is added to the mixture. The mixture is extracted with chloroform. The chloroform solution is washed with water, dil. aqueous sodium hydroxide and then water and dried over magnesium sulfate. Chloroform is distilled off and the residue is purified by silica gel column chromatography (Wakogel C-200). The column is eluted with chloroform-methanol (50:1) to obtain methyl 4-(5-methyl-1,2,3,4-tetrazol-1-yl)butyrate (5.7 g) as colorless liquid.

Workup

  1. temperatureice-cooling
  2. stirringThe mixture is stirring at room temperature for 1.5 hours
  3. concentrationconcentrated to about 1/3 volume under reduced pressure
  4. stirringwith stirring
  5. temperatureice-cooling
  6. stirringThe mixture is stirred at room temperature for 1 hour
  7. temperaturegently refluxed for 2 hours
  8. concentrationThe reaction mixture is concentrated
  9. additionice-water is added to the mixture
  10. extractionThe mixture is extracted with chloroform
  11. washThe chloroform solution is washed with water, dil. aqueous sodium hydroxide
  12. dry with materialwater and dried over magnesium sulfate
  13. distillationChloroform is distilled off
  14. customthe residue is purified by silica gel column chromatography (Wakogel C-200)
  15. washThe column is eluted with chloroform-methanol (50:1)

Sources & evidence

ORD record
ord-dfc2d76aa02548b4b17db83273f07e55
Source dataset
uspto-grants-1983_02
Patent number
US04372953

Reaction notes

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