Butyl ether → N-(4-ethoxyphenyl)-2,5-dimethylaniline

HRID 2266977Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[CH2:10]([O:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1)[CH3:11].CC([O-])(C)C.[Na+].O(CCCC)CCCC>>[CH2:10]([O:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=2[CH3:9])=[CH:15][CH:14]=1)[CH3:11]

Participants

Reactant 4

HCID 8909Butyl ether

HCID 90764-Ethoxyaniline

HCID 32883Chloro-p-xylene

HCID 23676156Sodium t-butoxide

Product 1

HCID 57857510N-(4-ethoxyphenyl)-2,5-dimethylanilineYield 98%

Conditions

Temperature: 110 °C

Procedure

Following general procedure E, a mixture of 2-chloro-p-xylene (134 μL, 1.0 mmol), 4-ethoxyaniline (154 μL, 1.2 mmol), NaOt-Bu (115 mg, 1.2 mmol), 10 (0.08 mg, 0.01 mol %), 1 (0.05 mg, 0.01 mol %), and Bu2O (1 mL) was heated to 110° C. for 1 h. The crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-30% EtOAc/hexanes) to provide the title compound as a white solid (235 mg, 98%), mp 56-58° C. 1H NMR (300 MHz, CDCl3) δ: 7.10 (m, 3H), 6.95 (m, 3H), 6.72 (d, J=7.5 Hz, 1H), 5.26 (s, 1H), 4.09 (q, J=7.0 Hz, 2H), 2.33 (s, 3H), 2.29 (s, 3H), 1.51 (t, J=7.0 Hz, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 154.7, 143.5, 136.8, 136.5, 130.9, 122.5, 121.0, 116.1, 116.1, 115.6, 64.1, 21.6, 17.7, 15.3 ppm. IR (neat, cm−1): 3402, 2978, 2923, 1511, 1478, 1292, 1238, 1117, 1049, 798. Anal. Calcd. for C16H19NO: C, 79.63; H, 7.94. Found: C, 79.70; H, 8.01.

Workup

customThe crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-30% EtOAc/hexanes)

Sources & evidence

ORD record: ord-29b94ffb26c84de3be1290e9ed5918a8
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858784B2

Reaction notes

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