Triethylamine → 3,5-dichloro-4-(3-(N-(4-trifluoromethoxyphenyl)carbamoyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

HRID 323659Notes

Reaction equation

HRID 323659 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([O:15][CH2:16][CH:17]=[C:18]([Cl:20])[Cl:19])[CH:12]=[C:11]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=O.C(N(CC)CC)C.C(N=C=NCCCN(C)C)C.[F:40][C:41]([F:51])([F:50])[O:42][C:43]1[CH:49]=[CH:48][C:46]([NH2:47])=[CH:45][CH:44]=1>ClCCl>[Cl:21][C:11]1[CH:12]=[C:13]([O:15][CH2:16][CH:17]=[C:18]([Cl:20])[Cl:19])[CH:14]=[C:2]([Cl:1])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8](=[O:10])[NH:47][C:46]1[CH:48]=[CH:49][C:43]([O:42][C:41]([F:40])([F:50])[F:51])=[CH:44][CH:45]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6008484-(Trifluoromethoxy)anilineHCID 220067334-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyric acid

Product 1

HCID 220068693,5-dichloro-4-(3-(N-(4-trifluoromethoxyphenyl)carbamoyl)propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzeneYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.26 g of 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)-phenoxy)butyric acid and 0.07 g of triethylamine dissolved in 5 ml of dichloromethane was added dropwise 0.14 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (WSC) hydrochloride, while stirring under ice cooling. After stirring for 30 minutes, a solution of 0.12 g of 4-trifluoromethoxyaniline dissolved in 5 ml of dichloromethane was added dropwise. After stirring at room temperature for 12 hours, the reaction mixture was concentrated to give a residue. The residue was subjected to silica gel chromatography, which afforded 0.26 g of 3,5-dichloro-4-(3-(N-(4-trifluoromethoxyphenyl)carbamoyl)-propyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (70% yield), m.p., 88.8° C.

Workup

  1. stirringAfter stirring for 30 minutes
  2. additionwas added dropwise
  3. stirringAfter stirring at room temperature for 12 hours
  4. concentrationthe reaction mixture was concentrated
  5. customto give a residue

Sources & evidence

ORD record
ord-8e81e2ba7ffa43e2bc4fb195f85e7366
Source dataset
uspto-grants-2001_04
Patent number
US06214835B1

Reaction notes

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