Acetic Anhydride → HCID 14881376, compound

HRID 1608340Notes

Reaction equation

HRID 1608340 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].OCC[N:11]1[C:16]([CH3:17])=[C:15]([CH3:18])[N:14]=[C:13]([CH3:19])[C:12]1=[O:20]>N1C=CC=CC=1>[C:5]([O:4][CH2:1][CH2:2][N:11]1[C:16]([CH3:17])=[C:15]([CH3:18])[N:14]=[C:13]([CH3:19])[C:12]1=[O:20])(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 147735301-(2-Hydroxyethyl)-3,5,6-trimethylpyrazin-2(1H)-one

Product 1

HCID 14881376HCID 14881376, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (2 ml) was added under ice-cooling to compound 026 (0.91 g, 5 mM) dissolved in pyridine (10 ml), and stirred at room temperature for 1.5 hours. The reaction mixture was concentrated in vacuo and dilute aqueous K2CO3 was added thereto, the resultant mixture being extracted three times with chloroform. The extract was dried with anhydrous magnesium sulfate and concentrated in vacuo. The residue was charged on a column of silica-gel (Florisil, 60 g) packed with benzene and eluted with benzene-ethyl acetate (5:1) to obtain compound 061 (0.58 g, yield: 51.8%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and dilute aqueous K2CO3
  2. additionwas added
  3. extractionthe resultant mixture being extracted three times with chloroform
  4. dry with materialThe extract was dried with anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. additionThe residue was charged on a column of silica-gel (Florisil, 60 g)
  7. washeluted with benzene-ethyl acetate (5:1)

Sources & evidence

ORD record
ord-0e900a35f7e4440a83d0739fbf32b63f
Source dataset
uspto-grants-1989_09
Patent number
US04870176

Reaction notes

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