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

HRID 27685

반응식

HRID 27685 반응식
[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]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 17305O,O-diethyl phosphorochloridothioateHCID 178517852HCID 178517852, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6cc74639db9f4e78915ca333425b534f
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04223025

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