Potassium Carbonate → O,O-bis(6-fluoro-2-pyridinyl) ethylphosphonothioate

HRID 2049122

反応式

HRID 2049122 の反応式
[F:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[CH:4][CH:3]=1.[C:9](=[O:12])([O-])[O-].[K+].[K+].[CH2:15]([P:17](Cl)(Cl)=[S:18])[CH3:16]>Cl[Hg]Cl.C(#N)C>[CH2:15]([P:17](=[S:18])([O:12][C:9]1[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=1)[O:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=1)[CH3:16]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 61246ethyl phosphonothioic dichloride, anhydrousHCID 178516046HCID 178516046、化合物

生成物 1

HCID 54415562O,O-bis(6-fluoro-2-pyridinyl) ethylphosphonothioate収率 52%

試薬・触媒・溶媒 2

HCID 24085Mercuric Chloride触媒HCID 6342Acetonitrile溶媒

実験手順

Into a three liter flask were placed 523 grams (4.6 moles) of 6-fluoro-2-pyridinol, 638 grams (4.6 moles) potassium carbonate, 1.0 grams HgCl2 and two liters of acetonitrile. The mixture was stirred at 50°-55° C. for two hours and allowed to cooled. The mixture was stirred while 269 grams (2.1 moles) of ethylphosphonothioic dichloride was added dropwise. An exotherm from 25° C. to 55° C. was obtained. The mixture was stirred at 50° C. for five hours and allowed to cool. The insolubles were filtered off and the solvent removed under reduced pressure at 45° C. The resulting oil was taken up in 1.5 liters of methylene chloride and washed once with one liter of water, once with one liter of aqueous 2% NaOH and again with one liter of water. The product layer was dried over sodium sulfate, filtered and the solvent removed under reduced pressure at 45° C. The resulting oil was poured into 250 milliliters of cold n-hexane and stirred. The solid product was filtered off and dried to give a 52% yield of the desired O,O-bis(6 -fluoro-2-pyridinyl) ethylphosphonothioate, m.p. 46°-48° C. (compound No. 1).

後処理

  1. customInto a three liter flask were placed
  2. temperatureto cooled
  3. additionwas added dropwise
  4. customAn exotherm from 25° C. to 55° C. was obtained
  5. stirringThe mixture was stirred at 50° C. for five hours
  6. temperatureto cool
  7. filtrationThe insolubles were filtered off
  8. customthe solvent removed under reduced pressure at 45° C
  9. washwashed once with one liter of water, once with one liter of aqueous 2% NaOH and again with one liter of water
  10. dry with materialThe product layer was dried over sodium sulfate
  11. filtrationfiltered
  12. customthe solvent removed under reduced pressure at 45° C
  13. additionThe resulting oil was poured into 250 milliliters of cold n-hexane
  14. stirringstirred
  15. filtrationThe solid product was filtered off
  16. customdried

出典と根拠

ORDレコード
ord-2b313b096d3242528ec3f3add750907c
出典データセット
uspto-grants-1980_04
特許番号
US04196293

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