Chlorophenyl isocyanate → HCID 178518972, compound

HRID 2226252Notes

Reaction equation

HRID 2226252 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 78.1%

Procedure

2-Chlorophenylisocyanate (7 g) and trimethylsilyl azide (7.9 g) were mixed and heated under refluxing for eight hours. The excessive trimethylsilyl azide was distilled off under reduced pressure and to the residue there were added 40 ml of methanol. Thereafter, the methanol was evaporated and the residue was purified by flush column chlomatography (hexane:ethyl acetate=2:1) to obtain the desired 1-(2-chlorophenyl)-5(4H)-tetrazolinone (7 g) having a melting point in the range of from 124.5° to 125.5° C.

Workup

  1. temperatureheated
  2. temperatureunder refluxing for eight hours
  3. distillationThe excessive trimethylsilyl azide was distilled off under reduced pressure and to the residue there
  4. additionwere added 40 ml of methanol
  5. customThereafter, the methanol was evaporated
  6. customthe residue was purified
  7. customby flush column chlomatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-d4a2078f80cf4849ad577090be9300e4
Source dataset
uspto-grants-1994_09
Patent number
US05347010

Reaction notes

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