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Methanol → 3-(Phthalimidomethylthio)pyridine

HRID 274669
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HRID 274669 반응식
C[N:2]([CH3:12])[C:3]([S:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=O.[OH-:13].[Na+].C(N([CH2:20][CH3:21])CC)C.[CH3:22][OH:23]>C(O)C>[C:22]1(=[O:23])[N:2]([CH2:3][S:5][C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[C:12](=[O:13])[C:6]2=[CH:11][CH:10]=[CH:20][CH:21]=[C:7]12
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참가 물질

6

반응물 4

HCID 887MethanolHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 299059N,N-dimethyl-1-(pyridin-3-ylsulfanyl)formamide

생성물 1

HCID 190791383-(Phthalimidomethylthio)pyridine수율 80.9%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

To a solution of 1.00 g (5.49 mmol) of 3-(dimethylaminocarbonylthio)pyridine in 50 ml of methanol, 5.49 ml (5.49 mmol) of a 1N aqueous solution of sodium hydroxide was added. The mixture was heated at 60° C. for 1 hour with stirring. After cooling, the solvent was distilled off. The residue was dissolved in ethanol and dried. The solvent was distilled off. The residue thus obtained and 1.58 g of (6.59 mmol) of (N-bromomethyl)phthalimide were suspended in 50 ml of ethanol, and 0.92 ml (6.59 mmol) of triethylamine was added. The mixture was stirred at room temperature for 4 hours. The solvent was distilled off, and the residue was dissolved in chloroform, washed with water and dried. Then the solvent was distilled off. The residue was purified by column chromatography (eluent: hexane/ethyl acetate=1:1) to obtain powder. The powder thus obtained was washed with ether and dried to obtain 1.20 g of the desired compound (yield: 80.9%, colorless powder).

후처리

  1. temperatureAfter cooling
  2. distillationthe solvent was distilled off
  3. dissolutionThe residue was dissolved in ethanol
  4. customdried
  5. distillationThe solvent was distilled off
  6. customThe residue thus obtained
  7. stirringThe mixture was stirred at room temperature for 4 hours
  8. distillationThe solvent was distilled off
  9. dissolutionthe residue was dissolved in chloroform
  10. washwashed with water
  11. customdried
  12. distillationThen the solvent was distilled off
  13. customThe residue was purified by column chromatography (eluent: hexane/ethyl acetate=1:1)
  14. customto obtain powder
  15. customThe powder thus obtained
  16. washwas washed with ether
  17. customdried

출처 및 근거

ORD 기록
ord-9ed016b864a54d489a2aafd1a465af38
출처 데이터셋
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05389658

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