Acetic Anhydride → HCID 86026439, compound

HRID 643225Notes

Reaction equation

HRID 643225 reaction equation
[NH2:1][C:2]1[C:3](=[O:13])[O:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([NH2:12])=[CH:7][CH:6]=2.[C:14]1(=[O:20])O[C:17](=[O:18])[CH:16]=[CH:15]1.C(O[C:25](=[O:27])[CH3:26])(=O)C.[C:28]([O-])(=[O:30])[CH3:29].[Na+]>C(Cl)(Cl)Cl>[C:28]1(=[O:30])[N:1]([C:2]2[C:3](=[O:13])[O:4][C:5]3[C:10]([CH:11]=2)=[CH:9][C:8]([N:12]2[C:14](=[O:20])[CH:15]=[CH:16][C:17]2=[O:18])=[CH:7][CH:6]=3)[C:25](=[O:27])[CH:26]=[CH:29]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 517045Sodium AcetateHCID 15444379HCID 15444379, compound

Product 1

HCID 86026439HCID 86026439, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
4 °C

Procedure

Diamine 3 (200 mg, 1.14 mmol) and maleic anhydride (335 mg, 3.42 mmol) were placed in a dry 50-mL round bottom flask. Chloroform (11.5 mL) was added and the solution was heated to reflux for 20 h. The mixture was then filtered and the recovered solid was rinsed liberally with chloroform and then dried under vacuum. To this solid was added acetic anhydride (9 mL, 96 mmol) and sodium acetate (35 mg, 0.427 mmol) and the reaction was stirred vigorously for another 30 min. The mixture was then cooled to 4° C. for 4 h and filtered. The beige solid thus obtained was dried over vacuum to give compound 4 in 20% yield (76 mg, 0.226 mmol). mp: >296° C. (dec). FTIR (KBr) (cm−1): 1700, 1620. 1H-NMR (CDCl3): δ (ppm) 7.78 (s, 1H), 7.66 (dd, J=9.8 Hz, J=2.5 Hz, 1H), 7.63 (d, J=2.5 Hz, 1H), 7.50 (d, J=8.7 Hz, 1H), 6.93 (s, 2H), 6.91 (s, 2H). 13C-NMR (DMSO-d6): δ (ppm) 1699.99, 169.06, 156.80, 151.50, 143.62, 135.82, 134.89, 131.61, 128.63, 127.11, 118.60, 118.13, 117.58. HRMS: expected, 337.04630; found, 337.04605.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 20 h
  3. filtrationThe mixture was then filtered
  4. washthe recovered solid was rinsed liberally with chloroform
  5. customdried under vacuum
  6. filtrationfiltered
  7. customThe beige solid thus obtained
  8. customwas dried over vacuum

Sources & evidence

ORD record
ord-0c3df6bd064544faa3c5afa7a40e2149
Source dataset
uspto-grants-2010_04
Patent number
US07700375B2

Reaction notes

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