Dimethylformamide → HCID 19003325, compound

HRID 1654567Notes

Reaction equation

HRID 1654567 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:7][CH:6]([N:8]2[C:12](=[O:13])[C:11]3=[CH:14][C:15]([C:18]([OH:20])=[O:19])=[CH:16][CH:17]=[C:10]3[C:9]2=[O:21])[CH2:5][C:4]([CH3:23])([CH3:22])[NH:3]1.[CH2:25]1[O:33][CH:26]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CN(C)C=O>C(Cl)Cl>[CH3:22][C:4]1([CH3:23])[CH2:5][CH:6]([N:8]2[C:12](=[O:13])[C:11]3=[CH:14][C:15]([C:18]([O:20][CH2:25][CH:26]([OH:33])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:19])=[CH:16][CH:17]=[C:10]3[C:9]2=[O:21])[CH2:7][C:2]([CH3:24])([CH3:1])[NH:3]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7276Styrene OxideHCID 15217370HCID 15217370, compound

Product 1

HCID 19003325HCID 19003325, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 125 ml reaction flask equipped with a magnetic stirrer, thermometer, condenser and nitrogen atmosphere were placed the HALS of Example 1 (5.0 g, 0.015 mol), styrene oxide (1.6 g, 0.013 mol), Adogen™ 464 (Ashland Chemical Co.) (0.15 g) and 60 ml of dimethylformamide. The reaction was refluxed for 5 hours then cooled. The mixture was transferred to a separatory funnel with 100 ml methylene chloride and washed with 200 ml of 2.5% sodium hydroxide. Additional methylene chloride, 100 ml, was added and the solution extracted with two 100 ml portions of 5% sodium hydroxide and then 100 ml water. The organic solution was then dried with anhydrous magnesium sulfate and the solvent stripped using aspirator and high vacuum systems. The solid residue (2.9 g) was recrystallized from aqueous ethanol, then recrystallized again from methyl t-butyl ether/hexanes. After high vacuum removal of residual solvent, the product weighed 0.6 g and melted at 144°-146° C. The infrared spectrum (in chloroform) showed a broad carbonyl absorption at 1710 cm -1 (imide and ester). The structure of this material was further confirmed using proton NMR spectroscopy.

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 5 hours
  5. temperaturethen cooled
  6. washwashed with 200 ml of 2.5% sodium hydroxide
  7. additionAdditional methylene chloride, 100 ml, was added
  8. extractionthe solution extracted with two 100 ml portions of 5% sodium hydroxide
  9. dry with materialThe organic solution was then dried with anhydrous magnesium sulfate
  10. customThe solid residue (2.9 g) was recrystallized from aqueous ethanol
  11. customrecrystallized again from methyl t-butyl ether/hexanes
  12. customAfter high vacuum removal of residual solvent
  13. customa broad carbonyl absorption at 1710 cm -1 (imide and ester)

Sources & evidence

ORD record
ord-70c35c959eba4c05b8c91adeabca6325
Source dataset
uspto-grants-1995_04
Patent number
US05408008

Reaction notes

Loading…