Hydrochloric Acid → alpha,4-Dichloro-2-(benzoyl)benzenepropanenitrile

HRID 1995528Notes

Reaction equation

HRID 1995528 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].Cl[C:6]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9].CCOCC.[ClH:26]>C(#N)C.O>[Cl:26][CH:2]([CH2:3][C:6]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:7]=1[C:8](=[O:9])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:1]#[N:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 7855AcrylonitrileHCID 4581882,5-Dichlorobenzophenone

Product 1

HCID 13067144alpha,4-Dichloro-2-(benzoyl)benzenepropanenitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

A solution of 92.7 g (0.4 mole) of 2-amino-5-chlorobenzephenone 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

  1. additionWhen the addition
  2. extractionextracted with ether
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe ether solution was concentrated at reduced pressure
  5. customto give a brown oil, which

Sources & evidence

ORD record
ord-8f26102816fc4cac89072c06e5efc22a
Source dataset
uspto-grants-1983_09
Patent number
US04405518

Reaction notes

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