Formaldehyde → HCID 68835881, 화합물

HRID 47238

반응식

HRID 47238 반응식
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[C:7]1\[C:8](=[O:16])[NH:9][C:10]2[C:15]\1=[CH:14][CH:13]=[CH:12][CH:11]=2.[CH2:17]=O.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>CCO>[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:17][N:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7](=[CH:6][C:2]3[NH:1][CH:5]=[CH:4][CH:3]=3)[C:8]2=[O:16])[CH2:22][CH2:21]1

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 531671-MethylpiperazineHCID 5908088(Z)-3-((1H-pyrrol-2-yl)methylene)indolin-2-one

생성물 1

HCID 68835881HCID 68835881, 화합물수율 21%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

A mixture of Z-(1H-Pyrrol-2-ylmethylene)-1,3-dihydro-indol-2-one (120 mg, 0.57 mmol), paraformaldehyde (17 mg, 0.57 mmol), and 1-methylpiperazine (63 μL, 0.57 mmol) in 4.0 mL EtOH was heated at reflux for 6.5 h. After standing at room temperature for 23 h, the mixture was concentrated to 3 mL solvent and 1 mL of hexane added. The resulting solution was cooled to 0° C. and the yellow solid which formed was collected by filtration. The solid collected was partitioned between 30 mL dilute HCl and 20 mL Ethyl acetate. The organic layer was removed and the aqueous layer washed with ethyl acetate (15 mL). The aqueous layer was made basic to pH 8 with saturated NaHCO3 and extracted with ethyl acetate. The ethyl acetate layer was washed with H2O, brine and dried with Na2SO4. The organic layer was concentrated and the residue was crystallized from ethyl acetate/hexane to give the title compound (38 mg, 21%) as a bright yellow solid.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 6.5 h
  3. concentrationthe mixture was concentrated to 3 mL solvent and 1 mL of hexane
  4. additionadded
  5. customthe yellow solid which formed
  6. filtrationwas collected by filtration
  7. customThe solid collected
  8. customwas partitioned between 30 mL dilute HCl and 20 mL Ethyl acetate
  9. customThe organic layer was removed
  10. washthe aqueous layer washed with ethyl acetate (15 mL)
  11. extractionextracted with ethyl acetate
  12. washThe ethyl acetate layer was washed with H2O, brine
  13. dry with materialdried with Na2SO4
  14. concentrationThe organic layer was concentrated
  15. customthe residue was crystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-071b76b7dc524e829eb7e50af8cf8210
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699863B1

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