Diethyl Ether → alpha,4-Dichloro-2-(benzoyl)benzenepropanenitrile
Reaction equation
N[C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[C:17](#[N:20])[CH:18]=[CH2:19].[Cl:21]C1C=CC(Cl)=CC=1C(C1C=CC=CC=1)=O.CCOCC>C(#N)C.Cl.O>[Cl:21][CH:18]([CH2:19][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4](=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:17]#[N:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of 92.7 g (0.4 mole) of 2-amino-5-chlorobenzophenone in 250 ml of acetonitrile was added to a mixture of 70 g (0.52 mole) of cupric chloride, 65 g (0.63 mole) of t-butylnitrile, 500 ml of acrylonitrile, and 500 ml of acetonitrile. When the addition was complete stirring at room temperature was continued for 2 hr. The mixture was diluted with 80 ml of 6 N hydrochloric acid and 1500 ml of water, extracted with ether and dried over anhydrous sodium sulfate. The ether solution was concentrated at reduced pressure to give a brown oil, which contained the end product and 2,5-dichlorobenzophenone. Trituration of the oil with a mixture of ether and petroleum ether gave the end product as a tan solid. Recrystallization of a small portion of the end product from a mixture of ether and petroleum ether gave pale yellow needles, mp 69°-71°.
Workup
- additionWhen the addition
- extractionextracted with ether
- dry with materialdried over anhydrous sodium sulfate
- concentrationThe ether solution was concentrated at reduced pressure
- customto give a brown oil, which
Sources & evidence
- ORD record
- ord-e4c86cc5ec464ed89539a4f948ddef99
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04428878
Reaction notes
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