Water → 2,3-Dichloro-6-(trifluoromethyl)benzonitrile
Reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[C:3]=1[C:4]([NH2:6])=O.P(Cl)(Cl)(Cl)=O.O>C1C=CC=CC=1>[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([C:12]([F:15])([F:13])[F:14])[C:3]=1[C:4]#[N:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 35 °C
Procedure
To a solution of 229 g of 2,3-dichloro-6-trifluoromethylbenzamide in 2 liters of benzene was added 409 g of phosphorus oxychloride and then the mixture was heated at ref lux for 3.5 hours. After cooling, the solution was gradually added into 2 liters of water maintained at 30-40° C. to hydrolyze the excess phosphorus oxychloride therein and was allowed to separation. The aqueous layer was extracted with benzene, and the extract was combined with the organic layer previously obtained, washed with water and with saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled under reduced pressure, and the crude product obtained was washed with n-hexane and filtered to obtain 204 g of the title compound(mp. 53-54° C.).
Workup
- temperaturethe mixture was heated at ref lux for 3.5 hours
- temperatureAfter cooling
- customwas allowed to separation
- extractionThe aqueous layer was extracted with benzene
- custompreviously obtained
- washwashed with water and with saturated saline solution
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled under reduced pressure
- customthe crude product obtained
- washwas washed with n-hexane
- filtrationfiltered
Sources & evidence
- ORD record
- ord-bf5c0b36694746b98409c37ab334a751
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06054605
Reaction notes
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