Dichloromethane → N-(4-[1,3]dioxolan-2-yl-2,5-dimethylphenyl)acrylamide

HRID 2246514Notes

Reaction equation

HRID 2246514 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[C:11]([CH3:12])=[CH:10][C:9]([NH2:13])=[C:8]([CH3:14])[CH:7]=1.ClCCl.C(N(C(C)C)CC)(C)C.[C:27](Cl)(=[O:30])[CH:28]=[CH2:29]>O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[C:11]([CH3:12])=[CH:10][C:9]([NH:13][C:27](=[O:30])[CH:28]=[CH2:29])=[C:8]([CH3:14])[CH:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 57461076HCID 57461076, compound

Product 1

HCID 57461077N-(4-[1,3]dioxolan-2-yl-2,5-dimethylphenyl)acrylamideYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500 mL round-bottom flask was added crude 4-[1,3]dioxolan-2-yl-2,5-dimethylphenylamine (5.6 g, 29 mmol), dichloromethane (100 mL) and diisopropylethylamine (7.6 mL, 43.5 mmol). The resulting mixture was stirred at room temperature until the ingredients dissolved and then the mixture was cooled to 0° C. Acryloyl chloride (2.35 mL, 29 mmol) was then added dropwise over a 5 minute period. The reaction mixture was stirred at 0° C. to 5° C. for 1 hour and then water (50 mL) was added and stirring was continued for about 30 minutes at which time fine solids had formed. The mixture was filtered to collect the solids. The layers of the filtrate were then separated and the organic layer was concentrated under reduced pressure to dryness. Dichloromethane (50 mL) was added to the residue and this mixture was stirred until a free-flowing slurry developed. The slurry was filtered (using the same funnel used to collect the fine solids above) and the filter cake was washed with dichloromethane (10 mL) and dried to provide N-(4-[1,3]dioxolan-2-yl-2,5-dimethylphenyl)acrylamide (3.1 g, 97% purity) as a white to off-white solid.

Workup

  1. dissolutiondissolved
  2. temperaturethe mixture was cooled to 0° C
  3. stirringThe reaction mixture was stirred at 0° C. to 5° C. for 1 hour
  4. stirringstirring
  5. customfine solids had formed
  6. filtrationThe mixture was filtered
  7. customto collect the solids
  8. customThe layers of the filtrate were then separated
  9. concentrationthe organic layer was concentrated under reduced pressure to dryness
  10. additionDichloromethane (50 mL) was added to the residue
  11. stirringthis mixture was stirred until a free-flowing slurry
  12. filtrationThe slurry was filtered (
  13. customto collect the fine solids above) and the filter cake
  14. washwas washed with dichloromethane (10 mL)
  15. customdried

Sources & evidence

ORD record
ord-60b25ceb9a514fc793e95b5d2e6d1ab0
Source dataset
uspto-grants-2010_03
Patent number
US07687521B2

Reaction notes

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