Toluene → HCID 135621797, compound

HRID 846526

Reaction equation

HRID 846526 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[C:4]([F:11])[CH:3]=1.[N:12]([Si](C)(C)C)=[N+:13]=[N-:14].C1(C)C=CC=CC=1>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9](=[O:10])[NH:14][N:13]=[N:12]2)=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 78378AzidotrimethylsilaneHCID 45582034-Chloro-2-fluorophenyl isocyanate

Product 1

HCID 135621797HCID 135621797, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 17.1 grams (0.10 mole) of 4-chloro-2-fluorophenyl isocyanate and 20.0 grams (0.17 mole) of azidotrimethylsilane was heated under reflux for 16 hours. The reaction mixture was cooled to ambient temperature and 60 ml of toluene and 100 ml of water were added. The mixture was allowed to stand for two hours and the resultant solid collected by filtration. The filter cake was washed with petroleum ether to yield 14.5 grams of 1-(4-chloro-2-fluorophenyl)-1,4-dihydro-5H-tetrazol-5-one; m.p. 185°-187° C. The reaction was repeated several times.

Workup

  1. temperatureunder reflux for 16 hours
  2. filtrationthe resultant solid collected by filtration
  3. washThe filter cake was washed with petroleum ether

Sources & evidence

ORD record
ord-a4b596b4e33649ad8cef5419040e6c32
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Linked notes

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