1,2-Dichloroethane → HCID 86640907, compound

HRID 2192763Notes

Reaction equation

HRID 2192763 reaction equation
O[C:2]1C=CC(C(=O)C=[CH:8][C:9]2[CH:14]=[CH:13][C:12](OC)=[CH:11][CH:10]=2)=C[CH:3]=1.C(Cl)CCl.C1C=CC2N([OH:33])N=NC=2C=1.C(N(CC)CC)C.CN([CH:44]=[O:45])C>CO>[CH:9]12[CH2:8][CH:12]([CH:11]=[CH:10]1)[CH2:13][CH:14]2[C:44]([OH:45])=[O:33].[CH2:2]=[CH2:3]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 97793HCID 97793, compound

Product 1

HCID 86640907HCID 86640907, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 5-norbornene-2-carboxylic acid/ethylene copolymer (13.2 g, 79.64 mmol) that was polymerized in (2), 4′-hydroxy-4-methoxy chalcone (Aldrich, 18.4 g, 72.4 mmol), EDC (Aldrich, 22.2 g, 115.84 mmol), and HOBT (Aldrich, 14.7 g, 108.6 mmol) were put into the 2-neck flask having the volume of 250 ml, and then dissolved in 100 ml of DMF. After the temperature was reduced to 0° C., triethylamine (Aldrich, 50 ml, 362 mmol) was slowly dropped on the reaction solution. After the temperature was increased to normal temperature and maintained for 3 hours, when the reaction was finished, the reaction solution was dropped on a large amount of methanol to precipitate the polymer, and the polymer was filtered to obtain the 5-norbornene-2-(4′-hydroxy-4-methoxy chalcone)ester/ethylene copolymer to which the 1-(3-methoxy phenyl)-3-(2-hydroxyphenyl)-2-propenone functional group was introduced (yield: 82.5%).

Workup

  1. customwas reduced to 0° C.
  2. temperatureAfter the temperature was increased to normal temperature
  3. temperaturemaintained for 3 hours
  4. customto precipitate the polymer
  5. filtrationthe polymer was filtered

Sources & evidence

ORD record
ord-6427f75520b241a88623d5f4c71b7fb1
Source dataset
uspto-grants-2012_12
Patent number
US08329841B2

Reaction notes

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