Acetic Anhydride → HCID 20780238, compound

HRID 1293065Notes

Reaction equation

HRID 1293065 reaction equation
[Br-].[CH2:2]([O:4][C:5]([CH2:7][N:8]1[CH:12]=[CH:11][N+:10]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])=[C:9]1[NH2:22])=[O:6])[CH3:3].[C:23]([O-])(=O)[CH3:24].[Na+].C(OC(=O)C)(=O)C.C(=O)(O)[O-].[Na+]>>[CH2:2]([O:4][C:5]([C:7]1[N:8]2[CH2:12][CH2:11][N:10]([C:13]3[C:14]([CH3:21])=[CH:15][C:16]([CH3:20])=[CH:17][C:18]=3[CH3:19])[C:9]2=[N:22][C:23]=1[CH3:24])=[O:6])[CH3:3]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 178472619HCID 178472619, compound

Product 1

HCID 20780238HCID 20780238, compoundYield 41%

Conditions

Temperature
160 °C

Procedure

A mixture of 3-ethoxycarbonylmethyl-1-(2,4,6-trimethyl-phenyl)-2-aminoimidazolium bromide (1.0 g, 2.7 mmol), sodium acetate (0.55 g, 6.75 mmol) and acetic anhydride (5.0 mL) was heated at 160° C. for 12 hr. Upon cooling, the mixture was poured into a flask containing ice. While stirring, excess sodium bicarbonate was added to the above mixture in small portions, and the resulting mixture was stirred at room temperature for 6 hr. Then, the mixture was extracted with dichloromethane (2×40 mL). The organic extracts were washed with water and dried over anhydrous sodium sulfate. Solvents were removed in vacuo and the residue was subjected to chromatography using ethyl acetate/hexanes (1:4) as eluent to afford the title compound as a light yellow oil which solidified upon cooling (0.344 g, 41% yield). 1H NMR (CDCl3, 300 MHz) δ 6.89 (s, 2H), 4.32 (q, J=7.1 Hz, 2H), 4.36-4.26 (m, 2H), 4.15-4.08 (m, 2H), 2.39 (s, 3H), 2.26 (s, 3H), 2.20 (s, 6H), 1.35 (t, J=7.1 Hz, 3H). Mass spec.: 314.15 (MH+).

Workup

  1. temperatureUpon cooling
  2. additionthe mixture was poured into a flask
  3. additioncontaining ice
  4. stirringthe resulting mixture was stirred at room temperature for 6 hr
  5. extractionThen, the mixture was extracted with dichloromethane (2×40 mL)
  6. washThe organic extracts were washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customSolvents were removed in vacuo

Sources & evidence

ORD record
ord-34da28c788e64008991626af58884533
Source dataset
uspto-grants-2007_07
Patent number
US07238699B2

Reaction notes

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