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

HRID 1445838
Notes
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Reaction equation

HRID 1445838 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 11451238Methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl ester2×

Product 1

HCID 68703272{2-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-diethyl-amineYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. washAdd dichloromethane and wash the crude organic layer with saturated sodium chloride solution
  2. dry with materialDry the organic extracts over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes