Methylamine → 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(methylamino)butyloxy)benzene

HRID 618403Notes

Reaction equation

HRID 618403 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:15][CH2:16][CH:17]=[C:18]([Cl:20])[Cl:19])[CH:5]=[C:6]([Cl:14])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12]Br.[CH3:21][NH2:22].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CN(C)C=O.CO>[Cl:1][C:2]1[CH:3]=[C:4]([O:15][CH2:16][CH:17]=[C:18]([Cl:20])[Cl:19])[CH:5]=[C:6]([Cl:14])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:22][CH3:21]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 222571451-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-4-bromobutane

Product 1

HCID 220067993,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(methylamino)butyloxy)benzeneYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-bromobutyloxy)benzene, 4 ml of 40% methanol solution of methylamine, 0.33 g of potassium carbonate and N,N-dimethylformamide was stirred at room temperature for 24 hours. To the reaction mixture was added 100 ml of saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with 100 ml of ethyl acetate. The ethyl acetate layer was successively washed with 100 ml of saturated sodium hydrogen carbonate and saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated, which afforded 0.80 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(methylamino)butyloxy)benzene (89% yield), nD26.0 1.5545.

Workup

  1. extractionthe mixture was extracted with 100 ml of ethyl acetate
  2. washThe ethyl acetate layer was successively washed with 100 ml of saturated sodium hydrogen carbonate and saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-304dd1fb098a49fda636dc192215c8dd
Source dataset
uspto-grants-1999_09
Patent number
US05952386

Reaction notes

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