Dimethyl Sulfoxide → N-[(+/-)-2-[4-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl]isoxazolidine

HRID 543577Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1Cl.[OH:13][C:14]1[CH:29]=[CH:28][C:17]([O:18][CH:19]([CH3:27])[C:20]([N:22]2[CH2:26][CH2:25][CH2:24][O:23]2)=[O:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:6][C:7]=1[O:13][C:14]1[CH:15]=[CH:16][C:17]([O:18][CH:19]([CH3:27])[C:20]([N:22]2[CH2:26][CH2:25][CH2:24][O:23]2)=[O:21])=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 1,2-dichloro-3-(trifluoromethyl)benzene (21.5 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 130° C. for 3 hours. After the mixture was cooled, water and benzene were added thereto to form two layers. The organic layer thus 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-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl]isoxazolidine (39.9 g) as a pale brown crystalline solid. Recrystallization from a mixture of n-hexane and ethyl acetate afforded a white crystalline solid. m.p. 66.5°-67.5° C.

Workup

temperatureAfter the mixture was cooled
customto form two layers
customThe organic layer thus separated
washwas washed with 1 N aqueous sodium hydroxide solution
dry with materialwith water and dried over anhydrous sodium sulfate
customRemoval of the solvent
distillationby a distillation in vacuo

Sources & evidence

ORD record: ord-f4394d3b919b4a07927fca7bb89c5bfb
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04447259

Reaction notes

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