Toluene → 4-chloro-2-fluorophenyl-1,4-dihydro-5H-tetrazol-5-one

HRID 1608033Notes

Reaction equation

HRID 1608033 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 1356217974-chloro-2-fluorophenyl-1,4-dihydro-5H-tetrazol-5-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 17.1 g (0.10 mole) of 4-chloro-2-fluorophenyl isocyanate and 20.0 g (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 g 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-200511deae0d442ab969d2122214d089
Source dataset
uspto-grants-1989_09
Patent number
US04868321

Reaction notes

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