Triethylamine → HCID 23042139, compound

HRID 2166089Notes

Reaction equation

HRID 2166089 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:3]=1[C:4]([NH:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([F:17])([F:16])[F:15])=[O:5].[C:23](Cl)(Cl)=[S:24].C(N(CC)CC)C>C1(C)C=CC=CC=1.COC(C)(C)C>[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:3]=1[C:4]1[O:5][C:23](=[S:24])[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:15])([F:16])[F:17])[N:6]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 23042045HCID 23042045, compound

Product 1

HCID 23042139HCID 23042139, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

4.79 g (15 mmol) of 2,6-difluoro-N'-(α,α,α-trifluoro-o-tolyl)-benzhydrazide in 30 ml of toluene are treated with 1.98 g (17 mmol) of thiophosgene and the reaction mixture is heated at the reflux temperature for 5 hours. 4.8 ml (35 mmol) of triethylamine are then added dropwise at 45° C. while cooling and, after cooling, the mixture is stirred at room temperature for about 1 hour. The mixture is subsequently taken up in 100 ml of tert.butyl methyl ether and the solution is washed in each case once with dilute, ice-cold sodium hydroxide solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue is purified by chromatography using acetone/n-hexane (1:4) as the eluent and crystallized from diisopropyl ether/n-hexane. In this manner there is obtained 5-(2,6-difluorophenyl)-3-(α,α,α-trifluoro-o-tolyl)-1,3,4-oxadiazole-2(3H) -thione as a white crystallizate, m.p. 128°-130° C.; mass spectrum: 358(58), 298(15 ), 289(17), 159(100).

Workup

  1. temperaturethe reaction mixture is heated at the reflux temperature for 5 hours
  2. temperaturewhile cooling
  3. temperatureafter cooling
  4. washthe solution is washed in each case once
  5. additionwith dilute
  6. dry with materialice-cold sodium hydroxide solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue is purified by chromatography
  9. customcrystallized from diisopropyl ether/n-hexane

Sources & evidence

ORD record
ord-31cf73efbc9b405bae325600f57d2e29
Source dataset
uspto-grants-1990_07
Patent number
US04943583

Reaction notes

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