Triethylamine → HCID 86754492, compound

HRID 377701Notes

Reaction equation

HRID 377701 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=O)=[CH:5][CH:4]=1.C(N(CC)CC)C.C(N=C=NCCCN(C)C)C.[Cl:34][C:35]1[CH:36]=[C:37]([O:46][CH2:47][CH:48]=[C:49]([Cl:51])[Cl:50])[CH:38]=[C:39]([Cl:45])[C:40]=1[O:41][CH2:42][CH2:43][NH2:44]>ClCCl>[Cl:34][C:35]1[CH:36]=[C:37]([O:46][CH2:47][CH:48]=[C:49]([Cl:51])[Cl:50])[CH:38]=[C:39]([Cl:45])[C:40]=1[O:41][CH2:42][CH2:43][NH:44][C:9](=[O:11])[CH:8]=[CH:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:14])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 749403-[4-(Trifluoromethyl)phenyl]prop-2-enoic acidHCID 220067523,5-Dichloro-4-(2-aminoethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

Product 1

HCID 86754492HCID 86754492, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.15 g of 4-trifluoromethylcinnamic acid and 0.07 g of triethylamine dissolved in 5 ml of dichloromethane was added 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 0.20 g of 3,5-dichloro-4-(2-aminoethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene 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 0.20 g of 3,5-dichloro-4-(2-(4-trifluoromethylcinnarnamido)ethoxy)-1-(3,3-dichloro-2-propenyloxy)benzene (63% yield), m.p., 109.4° 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-84b1e868c64d48088594ad664cbfd83e
Source dataset
uspto-grants-2000_02
Patent number
US06028100

Reaction notes

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