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Triethylamine → 3-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-tert-butyl-2,3-dihydro-1,3,4-oxadiazole-2-one

HRID 893314
Notes
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Reaction equation

HRID 893314 reaction equation
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([Cl:23])[C:14]=1[NH:24][NH:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].C(N(CC)CC)C>>[CH3:29][C:27]([C:26]1[O:31][C:1](=[O:2])[N:24]([C:14]2[C:13]([Cl:12])=[CH:18][C:17]([C:19]([F:20])([F:22])[F:21])=[CH:16][C:15]=2[Cl:23])[N:25]=1)([CH3:28])[CH3:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 15279907N'-(2,6-dichloro-4-trifluoromethylphenyl)-2,2-dimethylpropionhydrazideHCID 19083224Phosgen toluene

Product 1

HCID 198922363-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-tert-butyl-2,3-dihydro-1,3,4-oxadiazole-2-oneYield 45.1%

Conditions

Temperature
80 °C

Procedure

In 4.6 ml (8.9 mmols) of 20% phosgene-toluene solution, 0.33 g (1 mmol) of N'-(2,6-dichloro-4-trifluoromethylphenyl)-2,2-dimethylpropionhydrazide was heated to reflux for 16 hours (inner temperature of 80° C.). Then, an excess of phosgene and toluene was distilled off. After the residue was dissolved in 5 ml of methylene chloride, 0.65 g (6.4 mmols) of triethylamine was added to the solution and the mixture was heated to reflux for 30 minutes. Next, the mixture was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The thus obtained crude product was subjected to silica gel column chromatography to give 0.16 g of 5-(1,1-dimethylethyl)-3-(2,6-dichloro-4-trifluoromethylphenyl)-1,3,4-oxadiazolin-2-one.

Workup

  1. distillationThen, an excess of phosgene and toluene was distilled off
  2. dissolutionAfter the residue was dissolved in 5 ml of methylene chloride
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 30 minutes
  5. washNext, the mixture was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe thus obtained crude product

Sources & evidence

ORD record
ord-ab1524075eee422fb0525349ba4269b8
Source dataset
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05124341

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes