Hydrochloric Acid → 1-(3-Chlorophenyl)-1,2-dihydro-5H-tetrazol-5-one

HRID 2234820Notes

Reaction equation

HRID 2234820 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:9][C:10]1[CH:11]=[C:12]([N:16]=[C:17]=[O:18])[CH:13]=[CH:14][CH:15]=1.N([O-])=O.[Na+].Cl>O.CN(C=O)C>[Cl:9][C:10]1[CH:11]=[C:12]([N:16]2[C:17](=[O:18])[NH:3][N:2]=[N:1]2)[CH:13]=[CH:14][CH:15]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 17968Benzene, 1-chloro-3-isocyanato-HCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 23668193Sodium Nitrite

Product 1

HCID 1354088701-(3-Chlorophenyl)-1,2-dihydro-5H-tetrazol-5-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

DMF (5.0 ml) was cooled to 0° C. and stirred as 0.48 gram (0.0074 mole) of sodium azide was added. To this mixture was added 50 milligrams of aluminum chloride. The mixture was heated to 70° C. for 15 minutes, then the known compound 3-chlorophenylisocyanate was added neet in one portion. The mixture was heated at 75° C. for 3 hours and then cooled and poured into 100 ml of water containing 0.5 gram of sodium nitrite and 50 grams ice. To this was slowly added sufficient 10% hydrogen chloride to cause a change in KI/starch test paper. The resulting solid was filtered and dried. The filtrate was dissolved in ethyl acetate, washed with water and concentrated to a residue. The crude residue was purified with column chromatography on silica gel using 95:5 dichloromethane-methanol as an eluant yielding 0.38 gram of 1-(3-chlorophenyl)-tetrazolin-5-one.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated at 75° C. for 3 hours
  3. temperaturecooled
  4. filtrationThe resulting solid was filtered
  5. customdried
  6. dissolutionThe filtrate was dissolved in ethyl acetate
  7. washwashed with water
  8. concentrationconcentrated to a residue
  9. customThe crude residue was purified with column chromatography on silica gel using 95:5 dichloromethane-methanol as an eluant

Sources & evidence

ORD record
ord-ef085095a68b40f082d224665c99595f
Source dataset
uspto-grants-2010_05
Patent number
US07713970B2

Reaction notes

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