Dipropargylamine → 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(N,N-dipropargylcarbamoyl)butyloxy)benzene

HRID 323668Notes

Reaction equation

HRID 323668 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([O:16][CH2:17][CH:18]=[C:19]([Cl:21])[Cl:20])[CH:13]=[C:12]([Cl:22])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O.[CH2:23]([NH:26][CH2:27][C:28]#[CH:29])[C:24]#[CH:25].CCN=C=NCCCN(C)C.Cl>C(Cl)(Cl)Cl>[Cl:22][C:12]1[CH:13]=[C:14]([O:16][CH2:17][CH:18]=[C:19]([Cl:21])[Cl:20])[CH:15]=[C:2]([Cl:1])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9](=[O:11])[N:26]([CH2:27][C:28]#[CH:29])[CH2:23][C:24]#[CH:25]

Participants

5

Reactant 3

HCID 23350DipropargylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220067605-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)valeric acid

Product 1

HCID 220067843,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(N,N-dipropargylcarbamoyl)butyloxy)benzeneYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 0.20 g of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)-phenoxy)valeric acid and 0.05 g of dipropargylamine dissolved in 10 ml of chloroform was added 0.11 g of WSC hydrochloride, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was concentrated to give a residue. The residue was subjected to silica gel chromatography, which afforded 0.21 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(N,N-dipropargylcarbamoyl)butyl-oxy)benzene (92% yield), nD25.0 1.5481.

Workup

  1. stirringAfter stirring at room temperature for 24 hours
  2. concentrationthe reaction mixture was concentrated
  3. customto give a residue

Sources & evidence

ORD record
ord-2dac0eb773c64f5d8fd0d9c2e17faeb5
Source dataset
uspto-grants-2001_04
Patent number
US06214835B1

Reaction notes

Loading…