Dimethylformamide → 5-(3-Chloro-4-cyclohexylphenyl)-3-(4-(chloromethyl)phenyl)-1,2,4-oxadiazole

HRID 1777357Notes

Reaction equation

S(Cl)([Cl:3])=O.CN(C)C=O.[Cl:10][C:11]1[CH:12]=[C:13]([C:23]2[O:27][N:26]=[C:25]([C:28]3[CH:33]=[CH:32][C:31]([CH2:34]O)=[CH:30][CH:29]=3)[N:24]=2)[CH:14]=[CH:15][C:16]=1[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[OH-].[Na+]>ClCCl.O>[Cl:10][C:11]1[CH:12]=[C:13]([C:23]2[O:27][N:26]=[C:25]([C:28]3[CH:33]=[CH:32][C:31]([CH2:34][Cl:3])=[CH:30][CH:29]=3)[N:24]=2)[CH:14]=[CH:15][C:16]=1[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

Conditions

Temperature: 42.5 °C

Procedure

Thionyl chloride (0.27 mL, 0.0037 mol) and N,N-dimethylformamide (0.1 mL) are added to a stirred solution of {4-[5-(3-chloro-4-cyclohexylphenyl)-[1,2,4]-oxadiazol-3-yl]phenyl}methanol (0.45 g, 0.0012 mol) in dichloromethane (10 mL) at 0° C. The reaction mixture is heated at 40-45° C. and is stirred at this temperature for 1 hr. It is then cooled to 0-5° C. temperature, treated with demineralized water (3 mL) and is neutralized with 4N sodium hydroxide solution at 0-5° C. to adjust the pH 8-9. Finally it is extracted with dichloromethane (2×10 mL) and the combined extract is dried over sodium sulfate. Removal of solvent under reduced pressure gives 5-(3-chloro-4-cyclohexylphenyl)-3-(4-chloromethylphenyl)-[1,2,4]-oxadiazole.

Workup

temperatureIt is then cooled to 0-5° C. temperature
extractionFinally it is extracted with dichloromethane (2×10 mL)
extractionthe combined extract
dry with materialis dried over sodium sulfate
customRemoval of solvent under reduced pressure

Sources & evidence

ORD record: ord-7e87d024843f4897b496c197920f6b05
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266867B2

Reaction notes

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