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]Participants
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
- distillationThen, an excess of phosgene and toluene was distilled off
- dissolutionAfter the residue was dissolved in 5 ml of methylene chloride
- temperaturethe mixture was heated
- temperatureto reflux for 30 minutes
- washNext, the mixture was washed with water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe thus obtained crude product
Sources & evidence
- ORD record
- ord-ab1524075eee422fb0525349ba4269b8
- Source dataset
- uspto-grants-1992_06
- Patent number
- US05124341
Linked notes
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