Acrylonitrile → 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(ON=O)(C)(C)C.[C:24](#[N:27])[CH:25]=[CH2:26].[Cl:28]C1C=CC(Cl)=CC=1C(C1C=CC=CC=1)=O>C(#N)C.Cl.O.CCOCC>[Cl:28][CH:25]([CH2:26][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:24]#[N:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
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-butylnitrite, 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 6N 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-b1fc43d430d74d2fa44353e7524539c1
- Source dataset
- uspto-grants-1984_07
- Patent number
- US04460781
Reaction notes
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