Chlorophenyl isocyanate → HCID 178518972, compound

HRID 260894Notes

Reaction equation

HRID 260894 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=[O:10].C[Si]([N:15]=[N+:16]=[N-:17])(C)C>>[CH:5]1[CH:4]=[C:3]([N:8]2[NH:17][N:16]=[N:15][C:9]2=[O:10])[C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 76833Chlorophenyl isocyanateHCID 78378Azidotrimethylsilane

Product 1

HCID 178518972HCID 178518972, compoundYield 73.6%

Procedure

A mixture of 2-chlorophenylisocyanate (7 g) and trimethylsilyl azide (7.9 g) was refluxed under heating for either hours and then the mixture was evaporated to remove excess trimethylsilyl azide under reduced pressure distillation, followed by addition of methanol to the resulting residue. Thereafter, the methanol was distilled off 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 (6.6 g) having a m.p. in the range of from 124° to 125.5° C., in a yield of 73% of theory.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for either hours
  3. customthe mixture was evaporated
  4. customto remove excess trimethylsilyl azide
  5. distillationunder reduced pressure distillation
  6. additionfollowed by addition of methanol to the resulting residue
  7. distillationThereafter, the methanol was distilled off under reduced pressure
  8. customThe resulting residue was purified by flash column chromatography (eluent: hexane:ethyl acetate = 2:1)

Sources & evidence

ORD record
ord-3fcef35fa0ee4454a3b1ad854e1a5147
Source dataset
uspto-grants-1996_06
Patent number
US05530135

Reaction notes

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