Potassium Carbonate → O,O-dimethyl O-(3,5-dichloro-6-fluoro-2-pyridinyl) phosphorothioate

HRID 27684

반응식

HRID 27684 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-].[K+].[K+].[P:17](=[S:23])(Cl)([O:20][CH3:21])[O:18][CH3:19]>C(#N)C>[P:17](=[S:23])([O:10][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[C:5]([F:9])[N:4]=1)([O:20][CH3:21])[O:18][CH3:19]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 17304Dimethyl phosphorochloridothionateHCID 178517852HCID 178517852, 화합물

생성물 1

HCID 54251852O,O-dimethyl O-(3,5-dichloro-6-fluoro-2-pyridinyl) phosphorothioate수율 42.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

A mixture was prepared by admixing, with stirring, 20 grams (g) (0.11 mole (m)) of 3,5-dichloro-6-fluoro-2-pyridinol, 16 g (0.116 m) of potassium carbonate, 0.2 g of mercuric chloride and 250 milliliters (ml) of acetonitrile. To this mixture, with stirring, was added dropwise 16 g (0.1 m) of O,O-dimethyl phosphorochloridothioate. After the addition was complete, the mixture was stirred for an additional 0.5 hour and then heated to about 50° C., with stirring, for 2 hours. The reaction mixture was cooled to room temperature and filtered to remove insolubles. The solvent was removed by evaporation under reduced pressure. The residue was dissolved in 100 ml of benzene and washed with water. The organic layer was dried and filtered. The benzene was removed by evaporation. The residue (20 g of an oil) was crystallized from 30 ml of hexane to give 13 grams of O,O-dimethyl O-(3,5-dichloro-6-fluoro-2-pyridinyl) phosphorothioate. The product, a solid, melted at room temperature and had a refractive index of nd25 =1.5370. Upon analysis, the product was found to have carbon, hydrogen and nitrogen contents of 27.40, 2.28 and 4.27 percent, respectively, as compared with the theoretical contents of 27.46, 2.31 and 4.58 percent, respectively, as calculated for the above compound.

후처리

  1. customA mixture was prepared
  2. stirringTo this mixture, with stirring
  3. additionAfter the addition
  4. stirringthe mixture was stirred for an additional 0.5 hour
  5. stirringwith stirring, for 2 hours
  6. temperatureThe reaction mixture was cooled to room temperature
  7. filtrationfiltered
  8. customto remove insolubles
  9. customThe solvent was removed by evaporation under reduced pressure
  10. dissolutionThe residue was dissolved in 100 ml of benzene
  11. washwashed with water
  12. customThe organic layer was dried
  13. filtrationfiltered
  14. customThe benzene was removed by evaporation
  15. customThe residue (20 g of an oil) was crystallized from 30 ml of hexane

출처 및 근거

ORD 기록
ord-e3e11eee41c0425c9992023a47480474
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04223025

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