Dimethyl Sulfoxide → 2-[4-(2,4-Dichlorophenoxy)phenoxy]-1-(1,2-oxazolidin-2-yl)propan-1-one

HRID 543578Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1Br.[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:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:10][C:11]1[CH:12]=[CH:13][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:25][CH:26]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2,4-dichloro-bromobenzene (22.6 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. After the reaction mixture was cooled, water and benzene were added thereto 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-(2,4-dichlorophenoxy)phenoxy]propionyl]isoxazolidine (30.9 g) as a pale yellow crystalline solid. Recrystallization from a mixture of n-hexane/ethyl acetate yielded a white crystalline solid. m.p. 115°-118° C.

Workup

temperatureAfter the reaction mixture was cooled
customwhereby to form two layers
customThe organic layer so 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-048301d65148493ab7628b108ea59062
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04447259

Reaction notes

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