Dimethyl Sulfoxide → Isoxapyrifop

HRID 543579Notes

Reaction equation

HRID 543579 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[OH:10][C:11]1[CH:26]=[CH:25][C:14]([O:15][CH:16]([CH3:24])[C:17]([N:19]2[CH2:23][CH2:22][CH2:21][O:20]2)=[O:18])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C1C=CC=CC=1.O>[Cl:8][C:7]1[C:2]([O:10][C:11]2[CH:12]=[CH:13][C:14]([O:15][CH:16]([CH3:24])[C:17]([N:19]3[CH2:23][CH2:22][CH2:21][O:20]3)=[O:18])=[CH:25][CH:26]=2)=[N:3][CH:4]=[C:5]([Cl:9])[CH:6]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 27666Pyridine, 2,3,5-trichloro-HCID 132794342-(4-Hydroxyphenoxy)-1-(1,2-oxazolidin-2-yl)propan-1-one

Product 1

HCID 174656IsoxapyrifopYield 82%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2,3,5-trichloropyridine (18.3 g), N-[(±)-2-(4-hydroxyphenoxy)propionyl]isoxazolidine (23.7 g) which was prepared as in Example 3, anhydrous potassium carbonate (14.5 g) and dimethylsulfoxide (200 ml) was stirred at 120° C. for 4 hours. To the reaction mixture, after cooling, were added water and benzene whereby to form two layers. The organic layer so separated was washed with 1 N aqueous sodium hydroxide solution and then with water and dried over anhydrous sodium sulfate. Removal of the solvent by a distillation in vacuo gave N-[(±)-2-[4-(3,5-dichloro-2-pyridyloxy)phenoxy]propionyl]isoxazolidine (31.4 g) as a pale yellow crystalline solid. Recrystallization from a mixture of n-hexane/ethyl acetate yielded a white crystalline solid. m.p. 105.5°-107.5° C.

Workup

  1. temperatureTo the reaction mixture, after cooling
  2. customto form two layers
  3. customThe organic layer so separated
  4. washwas washed with 1 N aqueous sodium hydroxide solution
  5. dry with materialwith water and dried over anhydrous sodium sulfate
  6. customRemoval of the solvent
  7. distillationby a distillation in vacuo

Sources & evidence

ORD record
ord-c1070985be1d4f92a1bc8a85b45bc241
Source dataset
uspto-grants-1984_05
Patent number
US04447259

Reaction notes

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