Acetic Anhydride → HCID 15232944, compound

HRID 2379290Notes

Reaction equation

HRID 2379290 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])/[CH:23]=[CH:24]\[C:25]([OH:27])=O)([OH:3])=[O:2].C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+]>>[C:22]1(=[O:28])[N:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:1]([OH:3])=[O:2])[C:25](=[O:27])[CH:24]=[CH:23]1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 86747141HCID 86747141, compound

Product 1

HCID 15232944HCID 15232944, compoundYield 45%

Conditions

Temperature
100 °C

Procedure

A mixture of N-(17-carboxyheptadecyl)maleamic acid (400 mg, 1.01 mmoles), 2.83 ml of acetic anhydride, and anhydrous sodium acetate (41.0 rag, 0.50 mmoles) was heated at 100° C. with stirring for 1 hour. The reaction mixture was allowed to cool, then poured onto ice and stirred for 1 hour. The resulting mixture was extracted with chloroform. The separated organic layer was washed with water and then with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and isolated and purified by silica gel column chromatography [eluent: mixture of benzene and chloroform (volume ratio: 1:1)], to give 18-maleimidooctadecanoic acid (172 mg, 45%) having the following properties.

Workup

  1. temperatureto cool
  2. additionpoured onto ice
  3. stirringstirred for 1 hour
  4. extractionThe resulting mixture was extracted with chloroform
  5. washThe separated organic layer was washed with water
  6. dry with materialwith saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customisolated
  9. custompurified by silica gel column chromatography [eluent: mixture of benzene and chloroform (volume ratio: 1:1)]

Sources & evidence

ORD record
ord-a060aaca9f624165a9b862ec43181fdc
Source dataset
uspto-grants-1994_11
Patent number
US05360914

Reaction notes

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