Water → 1-(4-{3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)-propane-1,2-dione 1-(O-methyl-oxime)

HRID 2099932Notes

Reaction equation

HRID 2099932 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([O:25][CH2:26][CH:27]=[C:28]([Cl:30])[Cl:29])[CH:22]=[C:21]([Cl:31])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[N:19][OH:20])[C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=1.[C:32](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[CH3:32][O:20][N:19]=[C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][O:4][C:3]2[C:2]([Cl:1])=[CH:24][C:23]([O:25][CH2:26][CH:27]=[C:28]([Cl:30])[Cl:29])=[CH:22][C:21]=2[Cl:31])=[CH:10][CH:11]=1)[C:16](=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 866225881-(4-{3-[2,6-Dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)-propane-1,2-dione 1-oxime

Product 1

HCID 766082031-(4-{3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)-propane-1,2-dione 1-(O-methyl-oxime)

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.8 g of 1-(4-{3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)-propane-1,2-dione 1-oxime, 0.43 g of potassium carbonate and 0.26 g of methyl iodide are stirred in 10 ml of dimethylformamide at room temperature for 2 hours. The reaction mixture is poured into water and extracted with ethyl acetate. After concentration of the organic phase and purification over silica gel, the title compound is obtained. 1H-NMR (CDCl3) 300 MHz: 2.30 (m, 2H), 2.51 (s, 3H), 4.08 (s, 3H), 4.15 (t, 2H), 4.29 (t, 2H), 4.59 (d, 2H), 6.11 (t, 1H), 6.83 (s, 2H), 6.95 (d, 2H), 7.30 (d, 2H)

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter concentration of the organic phase and purification over silica gel

Sources & evidence

ORD record
ord-1049ca1c869549758b373a4d483a18e5
Source dataset
uspto-grants-2009_08
Patent number
US07569727B2

Reaction notes

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