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Methanol → 3-(Phthalimidomethylthio)pyridine

HRID 2210135
ノート
印刷プレビュー

反応式

HRID 2210135 の反応式
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
参加物反応条件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 887MethanolHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 299059N,N-dimethyl-1-(pyridin-3-ylsulfanyl)formamide

生成物 1

HCID 190791383-(Phthalimidomethylthio)pyridine収率 80.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-9a8d20fd0f594c93b42142f4df2fa298
出典データセット
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05457106

反応ノート

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