1,1,3-Trichloropropene → 2-(4-Chlorobenzyl)-2-(3,3-dichloro-2-propenyl)malononitrile

HRID 749533Notes

Reaction equation

HRID 749533 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][CH:7]([C:10]#[N:11])[C:8]#[N:9])=[CH:4][CH:3]=1.[H-].[Na+].[Cl:16][C:17]([Cl:21])=[CH:18][CH2:19]Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]([CH2:19][CH:18]=[C:17]([Cl:21])[Cl:16])([C:8]#[N:9])[C:10]#[N:11])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 173781,1,3-TrichloropropeneHCID 180822-((4-Chlorophenyl)methyl)propanedinitrileHCID 24758Sodium hydride

Product 1

HCID 222350292-(4-Chlorobenzyl)-2-(3,3-dichloro-2-propenyl)malononitrileYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using 0.50 g of (4-chlorobenzyl)malononitrile, 5 ml of N,N-dimethylformamide, 0.12 g of sodium hydride (60% in oil), and 0.30 ml of 1,1,3-trichloropropene, and according to the process described in the Production Example 1, there was obtained 0.52 g of 2-(4-chlorobenzyl)-2-(3,3-dichloro-2-propenyl)malononitrile (the present compound (20)).

Sources & evidence

ORD record
ord-22a181a11d7a45a08047880596fc5a86
Source dataset
uspto-grants-2008_07
Patent number
US07402691B2

Reaction notes

Loading…