Triethylamine → HCID 23042063, compound

HRID 2166087Notes

Reaction equation

HRID 2166087 reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[F:9][C:10]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:11]=1[C:12]([NH:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Br:22])=[O:13].C(N(CC)CC)C>O1CCOCC1>[Br:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N:15]1[N:14]=[C:12]([C:11]2[C:10]([F:9])=[CH:26][CH:25]=[CH:24][C:23]=2[F:27])[O:13][C:2]1=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 23042014HCID 23042014, compound

Product 1

HCID 23042063HCID 23042063, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.3 ml (19 mmol) of trichloromethyl chloroformate are added dropwise at 10°-20° C. to a mixture of 5.34 g (16 mmol) of 2,6-difluoro-N'-(o-bromophenyl)-benzhydrazide and 5.50 ml (40 mmol) of triethylamine in 35 ml of dioxan. The reaction mixture is heated at the reflux temperature for a further 3 hours and the solvent and excess reagent are subsequently distilled off under reduced pressure. The residue is taken up in diethyl ether and the solution is washed in each case once with water and sodium bicarbonate solution, dried over anhydrous sodium sulfate and evaporated under reduced pressure. After crystallization of the residue from acetone/n-hexane there is obtained pure 3-(2-bromophenyl)-5-(2,6-difluorophenyl)-1,3,4-oxadiazol-2(3H)-one, m.p. 111°-114° C.; IR spectrum: 1790 cm-1 ; mass spectrum: 354/352(15), 310/308(7), 171/169(41), 90(100).

Workup

  1. temperatureThe reaction mixture is heated at the reflux temperature for a further 3 hours
  2. distillationthe solvent and excess reagent are subsequently distilled off under reduced pressure
  3. washthe solution is washed in each case once with water and sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customAfter crystallization of the residue from acetone/n-hexane there

Sources & evidence

ORD record
ord-b8f51c6db1be4d9c86102d8eeb068497
Source dataset
uspto-grants-1990_07
Patent number
US04943583

Reaction notes

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