Diethylamine → {2-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-diethyl-amine

HRID 1445838Notes

Reaction equation

[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]([CH3:25])=[C:16]([CH2:18][CH2:19]OS(C)(=O)=O)[N:17]=2)=[CH:9][CH:8]=1>C1COCC1>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]([CH3:25])=[C:16]([CH2:18][CH2:19][N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[N:17]=2)=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Add diethyl amine (0.488 g, 6.68 mmol) to a solution of methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl ester (See Intermediate 13) (0.240 g, 0.668 mmol) in anhydrous THF (5 mL) in a sealed tube, and heat at 60° C. overnight. Add dichloromethane and wash the crude organic layer with saturated sodium chloride solution. Dry the organic extracts over Na2SO4, filter, and concentrate. Purify on silica gel eluting with 5% anmioniated methanol in dichloromethane to give {2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-diethyl-amine (0.150 g, 67%): MS (nme): 337 (M+1).

Workup

washAdd dichloromethane and wash the crude organic layer with saturated sodium chloride solution
dry with materialDry the organic extracts over Na2SO4
filtrationfilter
concentrationconcentrate
customPurify on silica gel eluting with 5%

Sources & evidence

ORD record: ord-bab867d79c6b499d9dea70013e583384
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666871B2

Reaction notes

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