Hydrochloric Acid → HCID 178518972, compound

HRID 260892Notes

Reaction equation

HRID 260892 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]=[C:17]=[O:18].N([O-])=O.[Na+].Cl>O.O1CCCC1>[CH:13]1[CH:12]=[C:11]([N:16]2[NH:7][N:6]=[N:5][C:17]2=[O:18])[C:10]([Cl:9])=[CH:15][CH:14]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 76833Chlorophenyl isocyanateHCID 6451240Aluminum(III) ChlorideHCID 23668193Sodium Nitrite

Product 1

HCID 178518972HCID 178518972, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Anhydrous aluminum chloride (1.5 g) was added to tetrahydrofuran (30 ml) with ice bath cooling, followed by a fifteen minute-stirring, addition of sodium azide (1.95 g) and 2-chlorophenylisocyanate (1.53 g) thereto and a sixteen hour-refluxing under heating in that order. After cooling, the reaction mixture was added with stirring to a mixture of sodium nitrite (2 g), water (200 ml) and ice (100 g) and the resulting mixture was acidified with 10% hydrochloric acid (until a potassium iodide starch paper became discolored), followed by extraction with ethyl acetate. The thus obtained ethyl acetate layer was washed with water, dried over sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by flash column chromatography (eluent: hexane: ethyl acetate = 2:1) to obtain the desired 1-(2-chlorophenyl)-5(4H)-tetrazolinone (1.41 g) having a m.p. in the range of from 124.5° to 125.5° C. in a yield of 72% of theory.

Workup

  1. temperaturecooling
  2. waitfollowed by a fifteen minute
  3. temperaturea sixteen hour-refluxing
  4. temperatureunder heating in that order
  5. temperatureAfter cooling
  6. additionthe reaction mixture was added
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe thus obtained ethyl acetate layer was washed with water
  9. dry with materialdried over sodium sulfate
  10. customevaporated under reduced pressure
  11. customThe resulting residue was purified by flash column chromatography (eluent: hexane: ethyl acetate = 2:1)

Sources & evidence

ORD record
ord-d6485ee7242142ad9f14f6b761bbf5eb
Source dataset
uspto-grants-1996_06
Patent number
US05530135

Reaction notes

Loading…