Triethylamine → HCID 131718104, compound

HRID 2255730Notes

Reaction equation

HRID 2255730 reaction equation
Cl.[CH3:2][C:3]1([CH3:25])[CH2:8][CH:7]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][C:16]([C:19](Cl)=[O:20])=[CH:17][CH:18]=[C:11]3[C:10]2=[O:22])[CH2:6][C:5]([CH3:24])([CH3:23])[NH:4]1.[CH2:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH2:34]([OH:37])[CH:35]=[CH2:36].C(N(CC)CC)C.[OH-].[Na+].[K+].[Br-]>C(Cl)Cl.CN(C)C=O>[CH2:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH2:13]([OH:14])[CH:12]=[CH2:11].[CH3:2][C:3]1([CH3:25])[CH2:8][CH:7]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][C:16]([C:19]([O:37][CH2:34][CH:35]=[CH2:36])=[O:20])=[CH:17][CH:18]=[C:11]3[C:10]2=[O:22])[CH2:6][C:5]([CH3:24])([CH3:23])[NH:4]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 168293Prop-2-en-1-ol--ethenylbenzene (1/1)HCID 253877Potassium BromideHCID 131718103HCID 131718103, compound

Product 1

HCID 131718104HCID 131718104, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Into a 125 ml reaction flask equipped with a magnetic stirrer, thermometer, condenser and nitrogen atmosphere were placed 5.0 g (0.013 mol) of acid chloride of Example 2 and 50 ml of 2% dimethylformamide in methylene chloride. This mixture was stirred during the addition of 2.9 g (about 0.013 hydroxy equivalents) of RJ-101 (a styrene/allyl alcohol copolymer from Monsanto having 7.7+.3 wt % hydroxy content). 2.8 g (0.028 mol) triethylamine were added. The reaction was refluxed for 1.5 hours. The mixture was transferred to a separatory funnel with 150 ml methylene chloride and 100 ml of 5% sodium hydroxide. The phases were separated and the organic phase was further extracted with three 50 ml portions of 5% sodium hydroxide and 50 ml water. The organic solution was dried with anhydrous magnesium sulfate and the solvent stripped using aspirator and high vacuum systems. The product was 4.3 g of light yellow crystals. The solid was redissolved in a minimum amount of methylene chloride and precipitated by dropwise addition to 800 ml of hexane. The solid was isolated by filtration yielding 3.9 g. The infrared spectrum (KBr pellet) showed the carbonyl absorption at 1715 cm-1 (imide and ester). The Tg was determined to be 87.6° C. Molecular weight data obtained from gel permeation chromatography indicated an Mn of 1400 and an Mw of 2100 (based on polystyrene standard). The NMR spectrum demonstrated the presence of the HALS moiety in the high molecular weight material (two singlets at 1.2 and 1.3 ppm) and the presence of aromatic hydrogens from the pendant phenyl groups.

Workup

  1. customInto a 125 ml reaction flask
  2. customequipped with a magnetic stirrer
  3. customthermometer, condenser and nitrogen atmosphere were placed
  4. temperatureThe reaction was refluxed for 1.5 hours
  5. customThe phases were separated
  6. extractionthe organic phase was further extracted with three 50 ml portions of 5% sodium hydroxide and 50 ml water
  7. dry with materialThe organic solution was dried with anhydrous magnesium sulfate
  8. dissolutionThe solid was redissolved in a minimum amount of methylene chloride
  9. customprecipitated by dropwise addition to 800 ml of hexane
  10. customThe solid was isolated by filtration
  11. customyielding 3.9 g
  12. customthe carbonyl absorption at 1715 cm-1 (imide and ester)
  13. customto be 87.6° C
  14. customMolecular weight data obtained from gel permeation chromatography

Sources & evidence

ORD record
ord-fb83a4ffe138489987f50cbb79ffeaf1
Source dataset
uspto-grants-1993_08
Patent number
US05241067

Reaction notes

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