Diphenyl Ether → N-[2-Methyl-6-(2-methylbutoxy)-4-pyridyl]ethane-1,2-diamine

HRID 333071Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([NH:8][CH2:9][CH2:10][NH2:11])[CH:5]=[C:4]([CH3:12])[N:3]=1.[Na].[CH3:14][CH:15]([CH2:18][CH3:19])[CH2:16][OH:17].C1(OC2C=CC=CC=2)C=CC=CC=1>CS(C)=O>[CH3:12][C:4]1[CH:5]=[C:6]([NH:8][CH2:9][CH2:10][NH2:11])[CH:7]=[C:2]([O:17][CH2:16][CH:15]([CH3:14])[CH2:18][CH3:19])[N:3]=1

Participants

Conditions

Temperature: 160 °C

Procedure

N-(2-Chloro-6-methyl-4-pyridyl)ethane-1,2-diamine (0.205 g, 1.2 mmol) was combined with the sodium salt of 2-methylbutan-1-ol (0.66 g, 6 mmol, that had been obtained by treating 2-methylbutan-1-ol with sodium hydride dispersion in THF), diphenylether (2.2 g) and DMSO (0.75 ml). The mixture was heated at 160° C. for 16 hours and purified by column chromatography (silica, ethyl acetate/methanol, 1% concentrated NH3) to yield 200 mg of a brown oil (0.84 mmol, 70%). MS (APCI) m/z=237.9 [M+1]+.

Workup

custompurified by column chromatography (silica, ethyl acetate/methanol, 1% concentrated NH3)

Sources & evidence

ORD record: ord-e156cebccf7442b09023dbb494268048
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877934B2

Reaction notes

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