Methane → 3'-Acetamidoacetophenone

HRID 1394388Notes

Reaction equation

HRID 1394388 reaction equation
[CH3:1][CH2:2][N:3]([C:21]([CH3:23])=[O:22])[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([C:10]2[N:15]3[N:16]=[CH:17][C:18]([C:19]#[N:20])=[C:14]3[N:13]=[CH:12][CH:11]=2)[CH:9]=1.C.[CH2:25]([OH:27])[CH3:26]>>[CH3:1][CH2:2][N:3]([C:21]([CH3:23])=[O:22])[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([C:10]2[N:15]3[N:16]=[CH:17][C:18]([C:19]#[N:20])=[C:14]3[N:13]=[CH:12][CH:11]=2)[CH:9]=1.[C:25]([C:8]1[CH:9]=[C:4]([NH:3][C:21](=[O:22])[CH3:23])[CH:5]=[CH:6][CH:7]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 297MethaneHCID 702EthanolHCID 5719Zaleplon

Product 2

HCID 5719ZaleplonHCID 3462023'-AcetamidoacetophenoneYield 82%

Conditions

Temperature
25 °C

Procedure

Zaleplon (22.8 g) is dissolved in ethanol (230 cm3) at reflux temperature then treated with charcoal (2.3 g, 10 m/m %). The solution is stirred for 10 minutes and filtered. The charcoal is washed with hot ethanol (20 cm3). The solution is cooled to 25° C. in 6 hours and kept at this temperature for 2 hours. Crystals are filtered and washed with ethanol (30 cm3). The product is dried under vacuum at 60° C. for 8 hours to afford zaleplon form 1 (18.7 g, 82%).

Workup

  1. temperatureat reflux temperature
  2. filtrationfiltered
  3. washThe charcoal is washed with hot ethanol (20 cm3)
  4. waitkept at this temperature for 2 hours
  5. filtrationCrystals are filtered
  6. washwashed with ethanol (30 cm3)
  7. customThe product is dried under vacuum at 60° C. for 8 hours

Sources & evidence

ORD record
ord-f17f626d9d5f42bcbe5391f7514bfe9f
Source dataset
uspto-grants-2008_03
Patent number
US07348429B2

Reaction notes

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