3-(Dimethylamino)prop-2-enenitrile → Fenpiclonil

HRID 1194115Notes

Reaction equation

HRID 1194115 reaction equation
Cl.[Cl:2][C:3]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5](=O)[CH2:6][NH2:7].C[N:15](C)[CH:16]=[CH:17][C:18]#N.CC[O-].[Na+].[Na]>C(O)C>[Cl:2][C:3]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]1[C:17]([C:16]#[N:15])=[CH:18][NH:7][CH:6]=1

Participants

6

Reactant 4

HCID 974973-(Dimethylamino)prop-2-enenitrileHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 22151845Ethanone, 2-amino-1-(2,3-dichlorophenyl)-, hydrochloride

Product 1

HCID 91724Fenpiclonil

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

20.0 g of 2,3-dichlorophenacylamine hydrochloride and 10.0 g of 3-dimethylaminoacrylonitrile are heated for 1 hour under reflux in 300 ml of ethanol. Then an ethanolic solution of sodium ethylate, prepared from 2.1 g of sodium and 30 ml of ethanol, is rapidly added dropwise and the reaction mixture is stirred for another 10 minutes under reflux. The reaction mixture is cooled to room temperature and then poured into ice/hydrochloric acid and the resultant mixture is stirred for 11/2 hours. The precipitate is isolated by filtration, washed with water and dried, affording 15.4 g (78% of theory) of title compound with a melting point of 152°-154° C.

Workup

  1. additionis rapidly added dropwise
  2. temperatureunder reflux
  3. customThe precipitate is isolated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-7271d8ee45af481180b9752a39f0a380
Source dataset
uspto-grants-1989_03
Patent number
US04812580

Reaction notes

Loading…