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Sulfuric Acid → N-(5-ethoxycarbonylmethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

HRID 1744043
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HRID 1744043 반응식
C([N:4]1[C:12]2[C:7](=[C:8]([CH3:27])[C:9]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:10]([CH3:20])[C:11]=2[NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:6][CH2:5]1)(=O)C.[O-]CC.[Na+].S(=O)(=O)(O)O.[OH-].[Na+]>C(OCC)(=O)C.C(O)C.O>[CH2:25]([O:24][C:22]([CH2:21][C:9]1[C:8]([CH3:27])=[C:7]2[C:12](=[C:11]([NH:13][C:14](=[O:19])[C:15]([CH3:17])([CH3:16])[CH3:18])[C:10]=1[CH3:20])[NH:4][CH2:5][CH2:6]2)=[O:23])[CH3:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 2723922Sodium ethoxideHCID 15524344N-(1-acetyl-5-ethoxycarbonylmethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

생성물 1

HCID 12112203N-(5-ethoxycarbonylmethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide수율 104.9%

시약·촉매·용매 3

HCID 702
Ethanol
용매
2회
HCID 962Water용매
HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of N-(1-acetyl-5-ethoxycarbonylmethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide obtained in Example 9 (3.5 g) and ethanol (35 ml) was added dropwise sodium ethoxide (20 wt % ethanol solution) while keeping the reaction temperature below 30° C., and the resulting mixture was refluxed for 1 hour. After cooling to 0–5° C., concentrated sulfuric acid (6.88 g, 7.5 equivalent) was added dropwise with stirring under cooling condition while keeping the reaction temperature below 30° C., and the resulting mixture was refluxed for 2 hours. Water (17.5 ml) was added to the reaction mixture, and ethanol was evaporated off in vacuo. To the residue obtained was added ethyl acetate (35 ml), and pH of the resulting mixture was adjusted with 25% aqueous sodium hydroxide solution (the aqueous layer was adjusted to pH 12–13), and the resulting mixture was partitioned between ethyl acetate and water. The separated organic layer was furthermore washed with water (35 ml). The washing and the aqueous layer separated above were combined and reextracted with ethyl acetate (35 ml). The extract and the organic layer separated above were combined and concentrated under reduced pressure to afford the title compound (3.26 g) as a crude product.

후처리

  1. customthe reaction temperature below 30° C.
  2. temperaturethe resulting mixture was refluxed for 1 hour
  3. temperatureAfter cooling to 0–5° C.
  4. temperatureunder cooling condition
  5. customthe reaction temperature below 30° C.
  6. temperaturethe resulting mixture was refluxed for 2 hours
  7. customwas evaporated off in vacuo
  8. customTo the residue obtained
  9. customwas partitioned between ethyl acetate and water
  10. washThe separated organic layer was furthermore washed with water (35 ml)
  11. customThe washing and the aqueous layer separated
  12. extractionThe extract
  13. customthe organic layer separated above
  14. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e422c7a5c1ab471298c36b5c68dc23ec
출처 데이터셋
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07012147B2

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