Hydrazoic acid → 5-(4-Chlorobutyl)-1-cyclohexyl-1H-tetrazole

HRID 1381919Notes

Reaction equation

HRID 1381919 reaction equation
[CH:1]1([NH:7][C:8](=O)[CH2:9][CH2:10][CH2:11][CH2:12][Cl:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)(Cl)Cl.[NH:21]=[N+:22]=[N-:23]>C1C=CC=CC=1>[Cl:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]1[N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:23]=[N:22][N:21]=1

Participants

5

Reactant 3

HCID 24530Hydrazoic acidHCID 24819Phosphorus pentachlorideHCID 116729745-Chloro-N-cyclohexylpentanamide

Product 1

HCID 112187395-(4-Chlorobutyl)-1-cyclohexyl-1H-tetrazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
18 °C

Procedure

A stirred solution of N-cyclohexyl-5-chloropentanamide (4.36 g, 0.020 mol) in benzene (30 ml) at 0° C. was treated with phosphorous pentachloride (4.4 g, 0.021 mol) in portions over 10 minutes. When the addition was complete the reaction was stirred for an additional 2 hours at 18° C. The solution was then cooled to 0° C. and treated with a solution of hydrazoic acid (0.04 mol) in benzene (50 ml) (prepared according to the method described in Reagents for Organic Synthesis, Volume 1, L. F. Fieser and M. Fieser, John Wiley and Sons (New York: 1967). The resulting solution was stirred at 0° C. for an additional 1.5 hours and at 18° C. for 48 hours and then heated under reflux for an additional 3 hours. The solvent was evaporated off under reduced pressure and the resulting residue was dissolved in ethyl acetate (250 ml). The resulting solution was washed with saturated aqueous sodium hydrogen carbonate (3×100 ml), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to yield a crude product. The crude product was purified by recrystallization from ethyl acetate-hexane to yield 5-(4-chlorobutyl)-1-cyclohexyl-1H-tetrazole as a colorless crystalline solid, having a melting point of 50°-51° C. and the following physical characteristics:

Workup

  1. additionWhen the addition
  2. temperatureThe solution was then cooled to 0° C.
  3. customprepared
  4. customdescribed in Reagents for Organic Synthesis, Volume 1, L
  5. stirringThe resulting solution was stirred at 0° C. for an additional 1.5 hours and at 18° C. for 48 hours
  6. temperatureheated
  7. temperatureunder reflux for an additional 3 hours
  8. customThe solvent was evaporated off under reduced pressure
  9. dissolutionthe resulting residue was dissolved in ethyl acetate (250 ml)
  10. washThe resulting solution was washed with saturated aqueous sodium hydrogen carbonate (3×100 ml)
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customto yield a crude product
  15. customThe crude product was purified by recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-32fbfa5912d44fc18199000b11646aca
Source dataset
uspto-grants-1989_02
Patent number
US04804658

Reaction notes

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