Sodium Carbonate → O,O-Diethyl O-(3,5-dichloro-6-fluoro-2-pyridinyl) phosphorothioate

HRID 27685

反応式

HRID 27685 の反応式
[Cl:1][C:2]1[C:3]([OH:10])=[N:4][C:5]([F:9])=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[P:17](=[S:25])(Cl)([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]>CN(C)C=O>[P:17](=[S:25])([O:10][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[C:5]([F:9])[N:4]=1)([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 17305O,O-diethyl phosphorochloridothioateHCID 178517852HCID 178517852、化合物

生成物 1

HCID 54005060O,O-Diethyl O-(3,5-dichloro-6-fluoro-2-pyridinyl) phosphorothioate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture was prepared by admixing, with stirring, 9.7 g (0.053 m) of 3,5-dichloro-6-fluoro-2-pyridinol, 5.6 g (0.053 m) of sodium carbonate and 100 ml of dimethylformamide. To this mixture was added all at once, at room temperature, with stirring, 9.9 g (0.053 m) of O,O-diethyl phosphorochloridothioate. The resulting mixture was heated at 60°-65° C. with stirring for one hour. The mixture was cooled to room temperature and filtered to remove insolubles. The solvent was removed by distillation under reduced pressure and the residue dissolved in 100 ml of benzene. The mixture was washed with water and the organic layer separated, dried and filtered. The benzene was removed by evaporation under reduced pressure. The residue (15 g) was crystallized from 15 ml of hexane giving 5.9 g of the desired O,O-diethyl O-(3,5-dichloro-6-fluoro-2-pyridinyl) phosphorothioate. The product melted at 31°-33° C. and upon analysis, was found to have carbon, hydrogen and nitrogen contents of 32.30, 3.30 and 4.19 percent, respectively, as compared with the theoretical contents of 32.36, 3.32 and 4.19 percent, respectively, as calculated for the above named compound.

後処理

  1. customA mixture was prepared
  2. additionTo this mixture was added all at once, at room temperature
  3. stirringwith stirring
  4. temperatureThe resulting mixture was heated at 60°-65° C.
  5. stirringwith stirring for one hour
  6. filtrationfiltered
  7. customto remove insolubles
  8. customThe solvent was removed by distillation under reduced pressure
  9. dissolutionthe residue dissolved in 100 ml of benzene
  10. washThe mixture was washed with water
  11. customthe organic layer separated
  12. customdried
  13. filtrationfiltered
  14. customThe benzene was removed by evaporation under reduced pressure
  15. customThe residue (15 g) was crystallized from 15 ml of hexane giving 5.9 g of the desired O,O-diethyl O-(3,5-dichloro-6-fluoro-2-pyridinyl) phosphorothioate

出典と根拠

ORDレコード
ord-6cc74639db9f4e78915ca333425b534f
出典データセット
uspto-grants-1980_09
特許番号
US04223025

関連ノート

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