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

HRID 1361726
ノート
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反応式

HRID 1361726 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 57461076HCID 57461076、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3974d741ae1943d4a86d158ac485bbf0
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07880010B2

反応ノート

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