Acetyl chloride → N-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-ylmethyl]-N-phenethyl-acetamide

HRID 1528740Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH2:14][NH:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[C:24](Cl)(=[O:26])[CH3:25].C(N(CC)CC)C>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH2:14][N:15]([CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:24](=[O:26])[CH3:25])=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 6367Acetyl chloride

HCID 8471Triethylamine

HCID 66577243[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-ylmethyl]-phenethyl-amine

Product 1

HCID 66578409N-[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-ylmethyl]-N-phenethyl-acetamide

Procedure

[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-ylmethyl]-phenethyl-amine (0.055 g, 0.15 mmol), acetyl chloride (0.05 mL, 0.75 mmol), and triethylamine (0.13 mL, 0.95 mmol) were combined and stirred at room temperature for 30 minutes. The mixture was loaded directly onto silica gel and purified by silica gel chromatography (30-50% EtOAc in hexanes) to give the title compound.

Workup

custompurified by silica gel chromatography (30-50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-c5b37981dca44b76b03e0330388c937a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090573B2

Reaction notes

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