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Potassium Carbonate → 5-[[5-[3-(2-Methyl-1,3-dioxolan-2-yl)propoxy]-2-nitrophenyl]methylene]-2,4-imidazolidinedione

HRID 867477
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HRID 867477 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=O.[CH2:13]1[O:22][C:16]([CH2:18][CH2:19][CH2:20]Cl)([CH3:17])[O:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].[O-]CC.[Na+].[O:33]=[C:34]1[NH:38][C:37](=[O:39])[CH:36](P(OCC)(=O)OCC)[NH:35]1>O.C(O)C.[I-].[K+].CN(C)C=O>[CH3:17][C:16]1([CH2:18][CH2:19][CH2:20][O:1][C:2]2[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:7]=[C:36]3[NH:35][C:34](=[O:33])[NH:38][C:37]3=[O:39])[CH:9]=2)[O:22][CH2:13][CH2:14][O:15]1
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참가 물질

10

반응물 5

HCID 11430Potassium CarbonateHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 800792-(3-Chloropropyl)-2-methyl-1,3-dioxolaneHCID 2723922Sodium ethoxideHCID 3516088Diethyl 5-hydantoylphosphonate

생성물 1

HCID 537342405-[[5-[3-(2-Methyl-1,3-dioxolan-2-yl)propoxy]-2-nitrophenyl]methylene]-2,4-imidazolidinedione
수율 84%

시약·촉매·용매 4

HCID 4875Potassium Iodide촉매HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

A mixture of 5-hydroxy-2-nitrobenzaldehyde (20.00 g, 0.12 mole), 5-chloro-2-pentanone ethylene ketal (21.7 g, 0.132 mole), potassium carbonate (20.00 g, 0.14 mole), potassium iodide (0.5 g) and dimethylformamide (200 mL) was heated with stirring at 120° C. After 4 hours, the mixture was cooled, diluted with water and extracted with diethyl ether. The combined ethereal extracts were washed with water, dried over magnesium sulfate and the solvent evaporated. The residual oil comprised of 5-[3-(2-methyl-1,3-dioxolan-2-yl)propoxy]-2-nitrobenzaldehyde (used without purification) was dissolved in ethanol (200 mL) and added in one portion to a solution of sodium ethoxide (10.05 g, 0.15 mole) and diethyl 2,4-dioxoimidazolidine-5-phosphonate (35.00 g, 0.15 mole) in ethanol (300 mL). The mixture was stirred at room temperature for 90 minutes, concentrated to a volume of approximate 300 mL and diluted with water. The yellow precipitate was filtered off, washed with water and dried in vacuo at 70° C. to give 5-[[5-[3-(2-methyl-1,3dioxolan-2-yl)propoxy]-2-nitrophenyl]methylene]-2,4-imidazolidinedione (38.01 g, 84%). An analytical sample was prepared by crystallization from ethanol and had m.p. 175°-180° C.

후처리

  1. temperaturewas heated
  2. temperaturethe mixture was cooled
  3. extractionextracted with diethyl ether
  4. washThe combined ethereal extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent evaporated
  7. dissolutionwas dissolved in ethanol (200 mL)
  8. stirringThe mixture was stirred at room temperature for 90 minutes
  9. concentrationconcentrated to a volume of approximate 300 mL
  10. additiondiluted with water
  11. filtrationThe yellow precipitate was filtered off
  12. washwashed with water
  13. customdried in vacuo at 70° C.

출처 및 근거

ORD 기록
ord-a41578fc11134582b8daf973efe503b8
출처 데이터셋
uspto-grants-1988_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04775674

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