Acetic Anhydride → HCID 19003304, compound

HRID 1654568Notes

Reaction equation

HRID 1654568 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:7][CH:6]([N:8]2[C:12](=[O:13])[C:11]3=[CH:14][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:17]=[C:10]3[C:9]2=[O:23])[CH2:5][C:4]([CH3:25])([CH3:24])[NH:3]1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>CN(C)C1C=CN=CC=1>[C:27]([N:3]1[C:4]([CH3:25])([CH3:24])[CH2:5][CH:6]([N:8]2[C:12](=[O:13])[C:11]3=[CH:14][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:17]=[C:10]3[C:9]2=[O:23])[CH2:7][C:2]1([CH3:1])[CH3:26])(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19003301HCID 19003301, compound

Product 1

HCID 19003304HCID 19003304, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Into a 125 ml reaction flask equipped with a magnetic stirrer, thermometer, condenser and nitrogen atmosphere were placed the HALS of Example 4 (0.9 g, 0.0025 mol), 4-dimethylaminopyridine (0.03 g) and 25 ml of acetic anhydride. The reaction was refluxed for 2 hours, then poured into a beaker containing 200 ml ice water. A brown oil separated immediately and the mixture was stirred until the oil solidified into a tan solid. This solid was isolated by filtration and washed on the filter funnel with several portions of water. The wet solid was dissolved in 50 ml methylene chloride and dried with anhydrous magnesium sulfate. The solvent was stripped to give 0.9 g of light tan crystals melting at 119°-121° C. The infrared spectrum (in chloroform) showed a broad carbonyl absorption at 1710 cm-1 (imide and ester) and an amide carbonyl at 1615 cm-1.

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 2 hours
  5. additionpoured into a beaker
  6. customA brown oil separated immediately
  7. customThis solid was isolated by filtration
  8. washwashed on the filter funnel with several portions of water
  9. dissolutionThe wet solid was dissolved in 50 ml methylene chloride
  10. dry with materialdried with anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-e6896763efa848d3b529c1ec25b4db99
Source dataset
uspto-grants-1995_04
Patent number
US05408008

Reaction notes

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